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[ CAS No. 4983-28-2 ] {[proInfo.proName]}

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Chemical Structure| 4983-28-2
Chemical Structure| 4983-28-2
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Quality Control of [ 4983-28-2 ]

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Product Details of [ 4983-28-2 ]

CAS No. :4983-28-2 MDL No. :MFCD09743796
Formula : C4H3ClN2O Boiling Point : No data available
Linear Structure Formula :- InChI Key :BOGPIHXNWPTGNH-UHFFFAOYSA-N
M.W : 130.53 Pubchem ID :14595700
Synonyms :

Calculated chemistry of [ 4983-28-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.06
TPSA : 46.01 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.08
Log Po/w (XLOGP3) : 0.81
Log Po/w (WLOGP) : 0.84
Log Po/w (MLOGP) : -0.45
Log Po/w (SILICOS-IT) : 1.22
Consensus Log Po/w : 0.7

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.71
Solubility : 2.52 mg/ml ; 0.0193 mol/l
Class : Very soluble
Log S (Ali) : -1.36
Solubility : 5.72 mg/ml ; 0.0439 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.66
Solubility : 2.88 mg/ml ; 0.0221 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 4983-28-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4983-28-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4983-28-2 ]

[ 4983-28-2 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 100-39-0 ]
  • [ 4983-28-2 ]
  • [ 138274-14-3 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h; <strong>[4983-28-2]2-Chloro-5-hydroxypyrimidine</strong> 34a (0.50 g, 3.8 mmol) was dissolved in N,N-dimethylformamide (5 mL).Benzyl bromide (0.55 mL, 4.6 mmol) and potassium carbonate (0.79 g, 5.7 mmol) were added, and the mixture was reacted at room temperature for 18 hours.The reaction was quenched with water (10 mL).It was extracted with ethyl acetate (20 mL) and the organic phase was washed with saturated sodium chlorideDry over anhydrous sodium sulfate, concentrate by suction filtration, and the residue obtained was purified by silica gel column chromatography[ethyl acetate/petroleum ether (v/v) = 1/10] purified,Get the title compound34b (0.76 g, yield 90percent) as a white solid.
89% With potassium carbonate; In methanol; at 20℃; for 14h; Example 9 Synthesis of 2-chloro-5-benzyloxy-pyrimidine Compound 31 Referring to the reaction scheme of , potassium carbonate (11.6 g, 84.3 mmol) was added to 10 g of the alcohol 40 (76.6 mmol) in 500 mL of MeOH, followed by benzyl bromide (10.1 mL, 84.3 mmol). After 14 hrs stirring at r.t., the reaction was stopped by addition of water (300 mL). MeOH was evaporated and the remaining aqueous layer was extracted with CHCl3. The combined CHCl3 layers were washed with brine, dried over magnesium sulfate, and filtered. Removal of the solvent followed by silica gel chromatography using 100:1 CHCl3:MeOH as eluent gave 15 g (89percent) of 2-amino-5-benzyloxy-pyrimidine (31) as a white solid. 1H NMR (CDCl3) delta 8.27 (s, 2H), 7.37-7.30 (m, 5H), 5.09 (s, 2H).
A solution of <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (70percent purity, 7.5g, 40mmol) in DMF (15mL, 190mmol), under argon, was cooled to 0°C. Cesium Carbonate (14. Og, 43mmol) was added, portionwise, and the mixture was stirred for 5min at 0°C then lOmin at r.t.. The mixture was cooled back back down to 0°C and benzyl bromide (5.1mL, 43mmol) was added, portionwise. The reaction was stirred at 0°C for 15min, then allowed to warm to r.t. and stirred for a further 90min. The solvent was removed in vacuo and the residue partitoned between EtOAc and water. The organic phase was separated, washed with water:brine(l : 1), dried (MgS04), and the solvent removed in vacuo. Trituration from a combination of Et20 and IH, and further trituration of the motherliquer after concentration in vacuo, afforded the title compound in two crops: RT = 3.54 min; m/z (ES ) = 221.0 [M+ H]+.
  • 2
  • [ 88987-42-2 ]
  • [ 4983-28-2 ]
  • [ 952582-03-5 ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 40℃; (2) Potassium carbonate (2.54 g) was added to a solution of 5-bromovaleric acid tert-butyl ester (4.3 g) obtained in Reference Example 1(1) above and 2-chloro- pyrimidin-5-ol (2 g) in dimethylsulfoxide (8.6 ml) and the mixture was stirred at 400C overnight. The reaction mixture was cooled to room temperature, water and ethyl acetate were added and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate = 49:1-->9:1) to give 5-(2-chloropyrimidin-5-yloxy)valeric acid tert-butyl ester (3.82 g). MS (m/z): 287/289 [M+H]+.
  • 3
  • [ 5445-17-0 ]
  • [ 4983-28-2 ]
  • [ 353292-84-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; Intermediate Production Example 1 Production of 2-chloro-5-[1-(methoxycarbonyl)ethoxy]pyrimidine Used in Production Example 1 A mixture of 0.17 g of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong>, 0.22 g of methyl 2-bromopropionate, 0.20 g of anhydrous potassium carbonate and 2.6 ml of N,N-dimethylformamide was stirred at 60° C. for 1 hour. The reaction solution was cooled to room temperature, then, poured into water, and extracted with t-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.17 g of 2-chloro-5-[1-(methoxycarbonyl)ethoxy]pyrimidine. 1H-NMR(CDCl3/300 MHz) delta(ppm): 1.68 (d, 3H, J=6.6 Hz),3.79(s, 3H), 4.82 (q, 1H, J=6.7 Hz), 8.27(s, 2H)
  • 4
  • [ 22536-65-8 ]
  • [ 4983-28-2 ]
YieldReaction ConditionsOperation in experiment
91% With hydrogen bromide; DL-methionine; In acetic acid; for 5h;Reflux; Prepare 1L four-necked flask with a stirring device and thermometer.Add 100 g of 2-chloro-5-methoxypyrimidine,300 mL of acetic acid was added to the reaction flask,Stir well, then add 153g of 48% hydrobromic acid and 1g of methionine.Warming up to reflux reaction for 5 h,Sampling HPLC controlled until the end of the reaction, product content 96%, dihydroxy by-product 0.5%;After dropping to room temperature, 300 mL of water was added to the reaction solution, and the mixture was extracted three times with 300 mL of dichloromethane.The organic phases were combined and washed with saturated sodium bicarbonate solution.Then, it is dried over anhydrous sodium sulfate, and after filtration, the organic phase is concentrated under reduced pressure to give a crude product;The crude product was recrystallized from the crude product to give a pale yellow solid, 82 g.The yield was 91% and the purity was 98%.
62% 2-Chloro-5-methoxypyrimidine (0.46 g, 3.18 mmol) in methylene chloride (10 mL) was treated with 1.0 N boron tribromide (16 mL, 16 mmol) at room temperature. The solution was stirred overnight. After this time the reaction was partitioned between saturated NaHCO3 and DCM. The aqueous layer was extraxted with additional DCM. The combined organic layers were dried (MgSO4), filtered, and concnetrated. The residue was purified by flash column chromatography on silica gel to give 0.26 g of compound 112A (62%): 1H NMR (DMSO-D6): delta 10.03 (s, IH), 8.30 (s, 2H), ESI (-)/MS: 129 (M-H)-.
61% With boron tribromide; In dichloromethane; at 20℃; for 20h; Intermediate 4: 2-Chloro-5-hydroxypyrimidineTo a solution of 2-chloro-5-methoxypyrimidine (lOg, 0.069mol) in dichloromethane (84mL) was added dropwise boron tribromide (104mL, 1M solution in dichloromethane) at -78C. The mixture was stirred at room temperature for 20h and then methanol (150mL) was added dropwise at -78C. The reaction mixture was concentrated under reduced pressure and the pH adjusted to 5 with aq. sodium hydroxide solution. The mixture was extracted with ethyl acetate and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure to give 2-chloro-5-hydroxypyrimidine (5.7g, 61%).Mass: (ES-) 129NMR: 5H (d6-DMSO) 8.27 (2H, s) and 10.85 (1H, br s).
55% Intermediate 4: 2-Chloro-5-hydroxypyrimidine To a solution of 2-chloro-5-methoxypyrimidine (lOg, 0.069mol) in dichloromethane (84mL) was added dropwise boron tribromide (104mL, 1M solution in dichloromethane) at -78C. The mixture was stirred at room temperature for 20h and then methanol (150mL) was added dropwise at -78C. The reaction mixture was concentrated under reduced pressure and the pH adjusted to 5 with aq. sodium hydroxide solution. The mixture was extracted with ethyl acetate and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure to give 2-chloro-5-hydroxypyrimidine (5.0g, 55%).Mass: (ES-) 129NMR: 5H (d6-DMSO) 8.27 (2H, s) and 10.85 (1H, br s).
27% With boron tribromide; In dichloromethane; at 0 - 20℃; for 16h; Boron tribromide (30mL) was slowly added to a solution of 2-chloro-5-methoxypyrimidine (2g, 13.83mmol) in DCM (lOmL) at 0 C. Allowed the reaction mass to stir at room temperature for 16h. Then the reaction mixture was slowly quenched with ice cold water, warmed to room temperature and diluted with DCM (lOOmL). The aqueous layer was separated and extracted with DCM (3x25mL). The organic phase was washed with brine, dried over Na2S04, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography to afford desired title compound (0.5g, 27%) as a solid. LCMS: m/z = 129.0 (M-H)+ (Negative mode).
With boron tribromide; In methanol; dichloromethane; carbon dioxide; Reference Example 25 To a solution of 2-chloro-5-methoxypyrimidine (1.90 g) which is previously prepared by a method disclosed in J. Chem, Soc., 4590 (1960) in methylene chloride (30 ml) is added dropwise boron tribromide (4.97 ml) over a period of 15 minutes in a dry ice/acetone bath. The mixture is stirred at room temperature for 22 hours, and thereto is added dropwise methanol (30 ml) in a dry ice/acetone bath. The reaction mixture is concentrated under reduced pressure, and the pH value thereof is adjusted to pH 5 with aqueous sodium hydroxide solution. The mixture is extracted twice with ethyl acetate, and the extract is washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to remove the solvent. The resulting crystals are washed with n-hexane to give 2-chloro-5-hydroxypyrimidine (1.47 g) as colorless crystals. M.p. 194-195 C.
Example 152(S)-2-(1-(5-(2,4-dichlorobenzyloxy)pyrimidin-2-yl)pyrrolidin-2-yl)acetic acid 152A. (S)-methyl 2-(1-(5-(2,4-dichlorobenzyloxy)pyrimidin-2-yl)pyrrolidin-2-yl)acetate: To a round bottom flask was added 2-chloro-5-methoxypyrimidine (250 mg, 1.73 mmol) and CH2Cl2 (1 mL). The reaction mixture was cooled to -78 C. and 1N BBr3 (4 eq) was added slowly over 15 min. The reaction mixture was slowly warmed to rt and was stirred ovn. The mixture was cooled to 0 C. and 1N BBr3 (4 eq) was added. The reaction was slowly warmed to rt and then stirred for 24 h. The reaction was quenched via addition of methanol at 0 C., and the mixture was evaporated to dryness. The residue was dissolved in water (1 mL) and the pH of the solution was adjusted to 5 using 1N NaOH solution. The resulting mixture was extracted with EtOAc (2×25 mL), and the combined organics were washed successively with water (20 mL) and brine (20 mL), and the organic layer was dried (MgSO4) and concentrated to give 2-chloropyrimidin-5-ol (170 mg, 75% yield). The crude product was dissolved in DMF (3 mL) and 2,4-dichloro-1-(chloromethyl)benzene (0.215 mL, 1.57 mmol), K2CO3 (270 mg, 1.96 mmol) were added. The reaction mixture was stirred at 60 C. for 4 h. The resulting solution was diluted with EtOAc (50 mL), and the organic layer was washed successively with water (4×30 mL) and brine (30 mL), and the organic layer was dried (MgSO4) and concentrated. The residue was purified via silica gel chromatography to give 2-chloro-5-(2,4-dichlorobenzyloxy)pyrimidine (310 mg, 81% yield) as white solid containing 50% of 2-bromo-5-(2,4-dichlorobenzyloxy)pyrimidine. The material was used as is in the subsequent step. To a microwave vial was added 2-chloro-5-(2,4-dichlorobenzyloxy)pyrimidine (54 mg, 0.19 mmol), (S)-methyl 2-(pyrrolidin-2-yl)acetate (80 mg, 0.56 mmol), Hunig's Base (0.16 mL, 0.93 mmol) and DMF (1.2 mL). The reaction was heated in a microwave at 180 C. for 30 min. The reaction mixture was diluted with MeOH, and the mixture was purified via preparative RP-HPLC to give 152A (clear oil, 40 mg, 0.101 mmol, 54.1% yield). LC-MS Anal. Calc'd for C18H19Cl2N3O3: 396.27. found [M+H] 396.2.

  • 5
  • [ 2746-23-8 ]
  • [ 4983-28-2 ]
  • 2-chloro-5-(thien-3-ylmethoxy)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N-methyl-acetamide; water; (2) A mixture of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong> (200 mg), 3-chloromethylthiophene (610 mg), potassium carbonate (635 mg) and dimethylformamide (3 ml) is stirred at 50° C. for one hour. After the reaction is complete, to the reaction mixture is added water, and extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=20:1-->20:3), and evaporated to remove the solvent to give 2-chloro-5-(3-thienylmethoxy)pyrimidine (345 mg) as colorless needles. M.p. 73°-76° C.
  • 6
  • [ 61187-16-4 ]
  • [ 4983-28-2 ]
  • 1-(β-naphthylmethyl)-4-(5-hydroxy-2-pyrimidinyl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In N-methyl-acetamide; water; EXAMPLE 8 To a mixture of 4.50 g. of 1-(beta-napthylmethyl)piperazine(as prepared in Example 7), 2.5 g. of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong> in 30 ml. of dimethylformamide is added 2.0 g. of sodium bicarbonate and the mixture is refluxed for six hours. The mixture is cooled and filtered and the filtrate concentrated to a small volume in vacuo. The concentrate is diluted with 100 ml. of water and the insoluble material is washed with water and hexane to yield 1-(beta-napthylmethyl)-4-(5-hydroxy-2-pyrimidinyl)piperazine.
  • 7
  • [ 2969-81-5 ]
  • [ 4983-28-2 ]
  • [ 945771-55-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; Reference Example 142-Chloropyrimidin-5-ol (3.89g) is dissolved in N,N- dimethylformamide (50ml) and thereto are added potassium carbonate (4.98g) and tert-butyl 4-bromo-butyrate (7.36g) and the mixture is stirred at room temperature overnight. To the reaction solution are added ethyl <n="169"/>acetate and water, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane : ethyl acetate - 24: 1-->4: 1) to give tert-butyl 4-(2-chloropyrimidin-5-yloxy)bromobutyrate (6.22g). MS (m/z): 273 [M+H]+
  • 8
  • [ 1895-39-2 ]
  • [ 4983-28-2 ]
  • [ 1192813-64-1 ]
YieldReaction ConditionsOperation in experiment
39.7% In water; N,N-dimethyl-formamide; at 90℃; for 24h; Step A: 2-Chloro-5-(Difluoromethoxy)pyrimidine 2-Chloropyrimidin-5-ol (1 g, 7.66 mmol) and sodium 2-chloro-2,2-difluoroacetate (3.50 g, 22.98 mmol) in N,N-dimethylformamide (20 mL) and water (0.2 mL) were heated to 90° C. for 24 hours and concentrated in vacuo. The residue was purified by column chromatography (5-30percent ethyl acetate/hexanes) to afford 2-chloro-5-(difluoromethoxy)pyrimidine (549 mg, 3.04 mmol, 39.7percent yield) as a pale yellow oil. MS (LC/MS) R.T.=1.32; [M+H]+=181.14.
39.7% In water; N,N-dimethyl-formamide; at 90℃; for 24h; Step A: 2-Chloro-5-(Difluoromethoxy)pyrimidine2-Chloropyrimidin-5-ol (1 g, 7.66 mmol) and sodium 2-chloro-2,2- difluoroacetate (3.50 g, 22.98 mmol) in N,N-dimethylformamide (20 mL) and water (0.2 mL) were heated to 90 °C for 24 hours and concentrated in vacuo. The residue was purified by column chromatography (5-30 percent ethyl acetate/hexanes) to afford 2- chloro-5-(difluoromethoxy)pyrimidine (549 mg, 3.04 mmol, 39.7 percent yield) as a pale yellow oil. MS (LC/MS) R.T. = 1.32; [M+H]+ = 181.14.
  • 9
  • [ 930-28-9 ]
  • [ 4983-28-2 ]
  • [ 1192813-80-1 ]
YieldReaction ConditionsOperation in experiment
54.6% With potassium carbonate; In N,N-dimethyl-formamide; Step A: 2-Chloro-5-(cyclopentyloxy)pyrimidine A mixture of <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (1 g, 7.66 mmol), chlorocyclopentane (2.39 mL, 22.98 mmol) and potassium carbonate (3.18 g, 22.98 mmol) in N,N-dimethylformamide were heated at 65° C. for 16 h at ambient temperature. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (0-25percent ethyl acetate/hexanes) to afford 2-chloro-5-(cyclopentyloxy)pyrimidine (831 mg, 4.18 mmol, 54.6percent yield) as a white solid. MS (LC/MS) R.T.=2.32; [M+H]+=199.23.
54.6% With potassium carbonate; In N,N-dimethyl-formamide; at 65℃; for 16h; A mixture of <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (1 g, 7.66mmol), chlorocyclopentane (2.39 ml., 22.98 mmol) and potassium carbonate (3.18 g, 22.98 mmol) in N,N-dimethylformamide were heated at 65° C. for 16 h at ambient temperature.Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo.The residue was purified by colunm chromatography (0-25percentethyl acetate/hexanes) to afford 2-chloro-5-(cyclopentyloxy)pyrimidine (831 mg, 4.18 mmol, 54.6percent yield) as a white solid.
  • 10
  • [ 56621-90-0 ]
  • [ 4983-28-2 ]
YieldReaction ConditionsOperation in experiment
25% With sulfuric acid; In water; for 2h;Reflux; Example 8 Synthesis of 2-chloropyrimidine-5-ol Compound 41 Referring to the reaction scheme of , Compound 40 (40 g, 0.31 mol) in 2N sulfuric acid was refluxed for 2 hrs. After cooling to r.t., the reaction mixture was extracted with EtOAc using continuous overnight liquid-liquid extraction. The combined EtOAc layers were washed with brine, dried over magnesium sulfate, and filtered. After solvent removal in vacuo and recrystallization with EtOH, 10 g (25percent) yellow solid 41 was obtained. 1H NMR (DMSO-d6) delta 10.93 (brs, 1H), 6.45 (t, J=4.88 Hz, 1H), 3.57 (t, J=4.4 Hz, 4H), 2.01-1.98 (m, 4H).
  • 11
  • [ 98961-97-8 ]
  • [ 4983-28-2 ]
  • [ 1146543-67-0 ]
  • 12
  • [ 1131870-25-1 ]
  • [ 4983-28-2 ]
  • [ 1245506-60-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 24h; A combination of (R)-methanesulfonic acid-3-[l-(3-isopropyl-[l,2,4]oxadiazol-5- yl)piperidin-4-yl]butyl ester (Preparation 3, 560mg, 1.62mmol), <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong> (423mg, 3.24mmol) and potassium carbonate (447mg, 3.24mmol) in DMF (4mL) was heated to 700C for 24h. The reaction mixture was diluted with water (75mL) and extracted with EtOAc (2 x 75mL). The combined organic fractions were washed with IM NaOH solution, then brine, and dried (MgSO4). Removal of the solvent in vacuo afforded the title compound: RT = 4.14 min; mlz (ES+) = 380.1 [M + H]+.
  • 13
  • [ 1245506-56-2 ]
  • [ 4983-28-2 ]
  • [ 1245506-57-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; A combination of (R)-methanesulfonic acid-3-[l-(5-chloropyrimidin-2-yl)piperidin-4- yl]butyl ester (Preparation 2, 641mg, 1.85mmol), <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong> (480mg, 3.69mmol) and potassium carbonate (510mg, 3.69mmol) in DMF (4mL) were heated at 800C until the reaction was complete. The mixture was diluted with water and extracted into EtOAc (x 3), then the organic fractions were combined, washed with IM NaOH solution, brine, and dried (MgSO4). Removal of the solvent in vacuo afforded the title compound: RT = 4.72 min; m/z (ES+) = 382.1 [M + H]+.
  • 14
  • [ 1245507-22-5 ]
  • [ 4983-28-2 ]
  • [ 1245507-21-4 ]
YieldReaction ConditionsOperation in experiment
To a solution of 4-(2-hydroxy-l-methylethyl)piperidine-l -carboxylic acid isopropyl ester (Preparation 111, 400mg, 1.74mmol) in DCM (8mL), under argon, was added triethylamine (316muL, 2.27mmol) and the mixture was cooled to 00C. Methanesulfonyl chloride (163muL, 2.09mmol) was added before stirring the reaction at this temperature for Ih. The mixture was diluted with DCM (5OmL), washed with IM HCl solution (5OmL), sat. NaHCO3 solution (5OmL), then brine (5OmL), and dried (MgSO4). Removal of the solvent in vacuo afforded the intermediate product 4-(2-methanesulfonyloxy-l-methylethyl)piperidine-l- carboxylic acid isopropyl ester: RT = 3.49 min; mlz (ES+) = 308.1 [M + H]+. To a solution of the product in THF (8mL), under argon, was added <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (249mg, 1.91mmol) followed by potassium carbonate (600mg, 4.34mmol), and the reaction was warmed to 500C for 16h. DMF (2mL) was added and the reaction heated to 55°C for 3 h. A further portion of DMF(2mL) was added and heating continued at 600C for 3 h. Further DMF (2mL) was added and the reaction stirred at 500C for 1Oh before being cooled to r.t. and the solvent removed in vacuo. The crude residue was partitioned between EtOAc (5OmL) and water (10OmL) and the organic phase was separated. The aqueous phase was extracted with EtOAc (5OmL) then the organic fractions were combined, washed with sat. NaHCO3 solution (5OmL), brine (5OmL), and dried(MgSO4). Removal of the solvent in vacuo afforded the title compound: 1H NMR deltaH (400MHz, CDCl3): 8.29 (s, 2H), 4.98 - 4.88 (m, IH), 4.29 - 4.12 (m, 2H), 4.02 - 3.86 (m, 2H), 2.78 - 2.64 (m, 2H), 1.96 - 1.84 (m, IH), 1.70 - 1.59 (m, 3H), 1.37 - 1.319 (m, 8H), 1.04 (d, /= 7.0 Hz, 3H).
  • 15
  • [ 1245506-67-5 ]
  • [ 4983-28-2 ]
  • [ 1245506-68-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 72h;Sealed tube; A combination of 4-((R)-3-methanesulfonyloxy-l-methylpropyl)piperidine-l- carboxylic acid isopropyl ester (Preparation 16, 300mg, 1.56mmol), 2-chloro-5- hydroxypyrimidine (213mg, 1.63mmol) and potassium carbonate (430mg, 3.11mmol) in DMF (5.OmL) were heated in a sealed tube to 700C for 72h. The reaction mixture was partitioned between EtOAc and brine and organic phase separated and dried (Na2SO4). Removal of the solvent in vacuo afforded the title compound: RT = 4.14 min m/z (ES+) = 356.1 [M + H]+.
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2-Chloro-5-methoxy-4-methylpyrimidine

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Chemical Structure| 1192813-64-1

[ 1192813-64-1 ]

2-Chloro-5-(difluoromethoxy)pyrimidine

Similarity: 0.79

Alcohols

Chemical Structure| 1395037-19-0

[ 1395037-19-0 ]

2,4-Dichloropyrimidin-5-ol

Similarity: 0.82

Chemical Structure| 26456-59-7

[ 26456-59-7 ]

Pyrimidin-5-ol

Similarity: 0.78

Chemical Structure| 55873-09-1

[ 55873-09-1 ]

2-Chloropyrimidin-4-ol

Similarity: 0.70

Chemical Structure| 143489-45-6

[ 143489-45-6 ]

2-Aminopyrimidin-5-ol

Similarity: 0.69

Chemical Structure| 1046816-75-4

[ 1046816-75-4 ]

(2-Chloropyrimidin-5-yl)methanol

Similarity: 0.69

Related Parent Nucleus of
[ 4983-28-2 ]

Pyrimidines

Chemical Structure| 22536-65-8

[ 22536-65-8 ]

2-Chloro-5-methoxypyrimidine

Similarity: 0.94

Chemical Structure| 1395037-19-0

[ 1395037-19-0 ]

2,4-Dichloropyrimidin-5-ol

Similarity: 0.82

Chemical Structure| 169677-66-1

[ 169677-66-1 ]

2-Chloro-5-(cyclopropylmethoxy)pyrimidine

Similarity: 0.82

Chemical Structure| 1245506-61-9

[ 1245506-61-9 ]

2-Chloro-5-methoxy-4-methylpyrimidine

Similarity: 0.79

Chemical Structure| 1192813-64-1

[ 1192813-64-1 ]

2-Chloro-5-(difluoromethoxy)pyrimidine

Similarity: 0.79

; ;