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[ CAS No. 628692-15-9 ] {[proInfo.proName]}

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Chemical Structure| 628692-15-9
Chemical Structure| 628692-15-9
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Product Details of [ 628692-15-9 ]

CAS No. :628692-15-9 MDL No. :MFCD03094664
Formula : C5H7BN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :YPWAJLGHACDYQS-UHFFFAOYSA-N
M.W : 153.93 Pubchem ID :2736778
Synonyms :

Calculated chemistry of [ 628692-15-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.35
TPSA : 75.47 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.59
Log Po/w (WLOGP) : -1.84
Log Po/w (MLOGP) : -1.99
Log Po/w (SILICOS-IT) : -1.62
Consensus Log Po/w : -1.21

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.69
Solubility : 31.1 mg/ml ; 0.202 mol/l
Class : Very soluble
Log S (Ali) : -0.52
Solubility : 46.1 mg/ml ; 0.299 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.66
Solubility : 34.1 mg/ml ; 0.221 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 628692-15-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 628692-15-9 ]

* 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 [ 628692-15-9 ]

[ 628692-15-9 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 1722-12-9 ]
  • [ 628692-15-9 ]
  • 2-methoxy-5-(2-pyrimidyl)pyrimidine [ No CAS ]
  • 2
  • [ 5332-24-1 ]
  • [ 628692-15-9 ]
  • 3-(2-methoxypyrimidin-5-yl)quinoline [ No CAS ]
  • 3
  • [ 13195-50-1 ]
  • [ 628692-15-9 ]
  • 2-methoxy-5-(5-nitrothien-2-yl)pyrimidine [ No CAS ]
  • 4
  • [ 4595-60-2 ]
  • [ 628692-15-9 ]
  • 2-methoxy-5-(2-pyrimidyl)pyrimidine [ No CAS ]
  • 6
  • [ 628692-15-9 ]
  • 2-[2-(3-iodo-phenyl)-2<i>H</i>-tetrazol-5-yl]-pyridine [ No CAS ]
  • 2-methoxy-5-[3-(5-pyridin-2-yl-tetrazol-2-yl)-phenyl]-pyrimidine [ No CAS ]
  • 7
  • [ 628692-15-9 ]
  • 2-[2-(3-fluoro-5-iodo-phenyl)-2<i>H</i>-tetrazol-5-yl]-pyridine [ No CAS ]
  • 5-[3-fluoro-5-(5-pyridin-2-yl-tetrazol-2-yl)-phenyl]-2-methoxy-pyrimidine [ No CAS ]
  • 8
  • [ 954123-48-9 ]
  • [ 628692-15-9 ]
  • 2-methoxy-5-(3-(((4-phenylpiperidin-4-yl)methoxy)methyl)-5-(trifluoromethyl)phenyl)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 1 2-Methoxy-5-(3-(((4-phenylpiperidin-4-yl)methoxy)methyl)-5-(trifluoromethyl)phenyl)pyrimidine. tert-Butyl 4-((3-bromo-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (60. 0 mg, 0.11 mmol), 2-methoxy-5-pyridine boronic acid (72.0 mg, 0.47 mmol), and tetrakis(triphenylphosphine) palladium(0) (17.1 mg, 0.011 mmol) were combined in dry tetrahydrofuran (2 mL) in a microwave tube and sealed. The mixture was flushed with nitrogen then 0.35 mL of a 1 N potassium hydroxide aqueous solution was introduced. The mixture was heated at 120° C. for 1 h via microwave. After cooling to room temperature, the reaction mixture was concentrated and treated with a trifluoroacetic acid/methylene chloride mixture (1:1, 2 mL) for 1 h. The solvent was removed in vacuo and the resulting crude mixture passed through a strong cation exchange column. After washing the column with several volumes of methanol, the product was eluted by washing the column with 2 M ammonia in methanol. Concentration and preparative HPLC afforded 21.0 mg (42percent) of the desired compound as its TFA salt. 1H-NMR (CDCl3, 500 MHz) delta 8.57 (s, 2H), 7.54 (s, 1H), 7.25-7.31 (m, 8H), 4.40 (s, 2H), 4.03 (s, 3H), 3.40 (s, 2H), 2.83-2.88 (m, 2H), 2.64-2.69 (m, 2H), 2.10-2.18 (m, 2H), 1.77-1.86 (m, 2H). Mass spec.: 458.18 (MH)+.
  • 9
  • [ 958852-14-7 ]
  • [ 628692-15-9 ]
  • [ 958852-15-8 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 8h; A mixture of 6-(methyloxy)-3-pyridinyl]boronic acid (225 mg, 1.5 mmol), 4- iodo-6-quinolinecarbaldehyde (283 mg, 1 mmol), tetrakistriphenylphosphine palladium (0) (57 mg, 0.05 mmol), 2 M aqueous K2CO3 (2.5 ml. of a 2 M solution), and dioxane (5 ml.) ) was heated at 100 0C for 8 h and cooled to room temperature. The dioxane was removed under reduced pressure and the residue dissolved in 2:1 mixture of methylene chloride/water and the solution filtered. The organic layer was separated and dried with sodium sulfate and the crude product obtained by decanting the solution and evaporation of the methylene chloride. The crude product was purified by silica gel chromatography eluting with methylene chloride/methanol (0-1percent methanol gradient) to give the title compound (250 mg, 95 percent). MS(ES)+ m/e 265 [M+H]+.
  • 10
  • [ 628692-15-9 ]
  • 3-(4-aminophenyl)-7-(2-methoxy-5-pyrimidinyl)thieno[3,2-c]pyridin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 133A 3-(4-aminophenyl)-7-(2-methoxy-5-pyrimidinyl)thieno[3,2-c]pyridin-4-amine The desired product was prepared by substituting 2-methoxy-5-pyrimidinylboronic acid for 4-pyridylboronic acid in Examples 121A-B. MS (ESI(+)) m/e 350 (M+H)+.
  • 11
  • [ 84249-14-9 ]
  • [ 628692-15-9 ]
  • C10H10N4O [ No CAS ]
  • 12
  • [ 867256-58-4 ]
  • [ 628692-15-9 ]
  • [4-(2-methoxy-pyrimidin-5-yl)-phenyl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 48h;Heating / reflux; To a stirred solution of (4-bromo-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl- pyrrolidin-l-yl)-methanone (100mg, 0.297mmol), sodium carbonate (94.4mg, 0.890mmol) and 2-Methoxy-5-pyrimidine boronic acid (230mg, 1.48mmol) in toluene (5ml), water (Iml) and ethanol (1.5ml) under nitrogen was added Tetrakis (triphenylphosphine) palladium (0) (34.3mg, 0.030mmol). The reaction was then heated to reflux for 48h. The reaction was allowed to cool and bound to a SCX-2 cartridge (5g). The cartridge was washed with two cartridge volumes of dimethylformamide and one volume of methanol. The product was eluted using 2M ammonia in methanol. The ammonia/methanol solution was evaporated on a Genevac HT4. The sample was further purified by prep-LCMS. The resulting acetonitrile/water fractions were combined and evaporated using a Genevac to give 51mg of a colourless oil (47percent). MS (ES+) 367.3
47% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 48h;Reflux; Inert atmosphere; Example 55[4-(2-Methoxy-pyrimidin-5-yl)-phenyl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone Procedure SS: To a stirred solution of (4-bromo-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone (100 mg, 0.297 mmol), sodium carbonate (94.4 mg, 0.890 mmol) and 2-Methoxy-5-pyrimidine boronic acid (230 mg, 1.48 mmol) in toluene (5 ml), water (1 ml) and ethanol (1.5 ml) under nitrogen was added Tetrakis (triphenylphosphine) palladium (0) (34.3 mg, 0.030 mmol). The reaction was then heated to reflux for 48 h. The reaction was allowed to cool and bound to a SCX-2 cartridge (5 g). The cartridge was washed with two cartridge volumes of dimethylformamide and one volume of methanol. The product was eluted using 2M ammonia in methanol. The ammonia/methanol solution was evaporated on a Genevac HT4. The sample was further purified by prep-LCMS. The resulting acetonitrile/water fractions were combined and evaporated using a Genevac to give 51 mg of a colourless oil (47percent). MS (ES+) 367.3
  • 13
  • [ 880770-31-0 ]
  • [ 628692-15-9 ]
  • 8-[3-(2-methoxy-pyrimidin-5-yl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 120℃; for 0.166667h;Microwave irradiation; Step-2 Preparation of 8-[3-(2-methoxy-pyrimidin-5-yl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinoline 43 In a microwave reaction tube, 8-(3-bromo-pyrrolo[2,3-b]pyridine-1-sulfonyl)-quinoline (44, 68 mg, 0.18 mmol), 2-methoxy-pyrimidine-4-boronic acid (67.4 mg, 0.438 mmol), and tetrakis(triphenylphosphine)palladium(0) (10 mg, 0.0088 mmol) were mixed in 1.0 M of potassium carbonate (0.52 mL) and tetrahydrofuran (0.84 mL). The resulting mixture was heated at 120° C. in a CEM Discover microwave unit for 10 minutes. Ethyl acetate and water were added and two layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine and dried over sodium sulfate. The product was concentrated under reduced pressure and the resultant crude material was purified by column chromatography (80-90percent ethyl acetate in hexane) to yield the desired product as a white solid (43, 0.005 g, 0.01 mmol). MS(ESI) [M+H+]+=417.8.
  • 14
  • [ 873663-39-9 ]
  • [ 628692-15-9 ]
  • 2-(3-acetamidophenyl)-4-(2-methoxypyrimidin-5-yl)-6-morpholinopyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 60℃; for 36h; A mixture of 2-(3-acetamidophenyl)-4-bromo-6-morpholinopyrimidine (0.037 g),<strong>[628692-15-9]2-methoxypyrimidin-5-ylboronic acid</strong> (0.019 g), tetrakis(triphenylphosphine)palladium(0)(3 mg), a saturated aqueous sodium bicarbonate solution (0.2 ml) and 1,2-dimethoxyethane(2 ml) was stirred and heated to 60°C for 18 hours under an atmosphere of nitrogen. A secondportion of each of <strong>[628692-15-9]2-methoxypyrimidin-5-ylboronic acid</strong> (0.019 g),tetrakis(triphenylphosphine)palladium(0) (2 mg), a saturated aqueous sodium bicarbonatesolution (0.2 ml) and 1,2-dimethoxyethane (1 ml) was added and the resultant mixture washeated to 60°C for a further 18 hours. The resultant reaction mixture was evaporated and theresidue was triturated under a 5:1 mixture (1 ml) of methylene chloride and methanol. Thesoluble material was purified by column chromatography on reversed-phase silica using an'Isolute SCX' column (1 g; International Sorbent Technology Limited, Mid Glamorgan, UK)by initially washing the column with methanol (5 ml) followed by elution with a 5:3:2 mixture of methanol, methylene chloride and a 7M methanolic ammonia solution. The material soobtained was dried under vacuum. There was thus obtained the title compound as a solid(0.034 g); NMR Spectrum: (DMSOd6) 2.05 (s, 3H), 3.66-3.8 (m, 8H), 3.97 (s, 3H), 7.3-7.37(m, 2H), 7.82 (d, 1H), 8.03-8.09 (m, 1H), 8.52 (s, 1H), 9.38 (s, 2H), 9.98 (s, 1H); MassSpectrum: M+HM07.
  • 15
  • [ 212267-75-9 ]
  • [ 628692-15-9 ]
  • N-[(2,6-dimethylphenyl)methyl]-2,3-dimethyl-6-[2-(methyloxy)-5-pyrimidinyl]imidazo[1,2-a]pyridin-8-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In water; N,N-dimethyl-formamide; at 100℃; for 2h;Microwave irradiation; Example 75;. iV-[(2,6-Dimethylphenyl)methyI]-2,3-dimethyl-6-[2-(methyIoxy)-5- pyrimidinyl] imidazo [1 ,2-a] pyridin-8-amine EPO <DP n="86"/>A mixture of 6-bromo-iV-[(2,6-dimethylphenyl)methyl]-2,3-dimethylimidazo[l ,2- alpha]rhoyridin-8-amine (500 mg, 1.39 mmol; WO 98/37080) and 2-methoxvpyrimidine-5- boronic acid (430 mg, 2.79 mmol) in 2M aqueous sodium carbonate (3 niL) and dimethylformamide (6 mL) was degassed with argon and then treated with [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium (10 mg, 0.01 mmol). The mixture was heated in an Initiator.(TM). Microwave Synthesizer at 100°C for 2 hours. The resulting reaction mixture was applied to an Isolute.(R). SCX cartridge. Elution with methanol, then 2M and 7M NH3 in methanol gave, after evaporation, the crude product which was further purified by silica gel chromatography eluting with ethyl acetate/hexane mixtures to yield the title compound. MS (ES+ve): [M+H]+ at m/z 388 (C23H25N5O requires [M+H]+ at m/z 388).
  • 16
  • 1-[3-(4-bromo-phenyl)-trans-cyclobutyl]-(2R)-2-methyl-pyrrolidine [ No CAS ]
  • [ 628692-15-9 ]
  • 2-methoxy-5-{4-[3-({2R}-2-methyl-pyrrolidin-1-yl)-trans-cyclobutyl]-phenyl}-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In isopropyl alcohol; at 90℃; for 5h; Example 16C; 2-Methoxy-5-{4-[3-({2R}-2-methyl-pyrrolidin-1-yl)-trans-cyclobutyl]-phenyl}-pyrimidine; To a solution of the product from Example 16B (50 mg, 0.17 mmol) in isopropyl alcohol (4 mL) under an atmosphere of nitrogen was added 2-methoxypyrimidine-5-boronic acid (Frontier Scientific, Inc., Logan, Utah, USA) (30 mg, 0.2 mmol), dichlorobis(triphenylphosphine)palladium(II) (6 mg, 8.5 mumol), and potassium carbonate (59 mg, 0.43 mmol). The mixture was heated at 90° C. for 5 hrs, cooled to ambient temperature and partitioned between ethyl acetate (25 mL) and H2O (10 mL). The organic extraction was washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed on silica gel eluting with 3percent (9:1 MeOH:concentrated NH4OH) in dichloromethane to provide 41 mg of the title compound. 1H NMR (300 MHz, CD3OD) delta 1.13 (d, J=6 Hz, 3H), 1.47 (m, 1H), 1.77 (m, 2H), 1.99 (m, 1H), 2.27 (m, 1H), 2.41 (m, 2H), 2.62 (m, 3H), 3.05 (m, 1H), 3.38 (m, 1H), 3.55 (m, 1H), 4.05 (s, 3H), 7.46 (d, J=9 Hz, 2H), 7.59 (d, J=9 Hz, 2H), 8.81 (s, 2H); (DCl/NH3) m/z 324 (M+H)+.
  • 17
  • [ 944058-81-5 ]
  • [ 628692-15-9 ]
  • 2-(2-methoxypyrimidin-5-yl)-4-(methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(I) thiophene-2-carboxylate; zinc diacetate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 130℃; for 0.75h;Microwave irradiation; The compounds shown in table 1 were prepared in an analogous manner to 4- (methylsulfonylmethyl)-6-morpholin-4-yl-2-thiophen-3-yl-pyrimidine (example 1), except where noted. Table 1Example 10: H NMR (300.132 MHz, DMSO) 53.19 (s, 3H), 3.72 (s, 8H), 4.01 (s, 3H),4.50 (s, 2H), 6.94 (s, IH), 9.38 (s, 2H) iPurification/Analysis details for examples 1 to 12:Dissolution Solvent 4 ml DMFInstrument Waters XBridge Prep, Cl 8 5 mum 100 x 19 mmColumn Phenomenex Gemini 5mu, Cl 8 100 x 21.2 mmFraction Trigger uv (at) 254 nmGradient 0 - 1 min 30percent MeCN, 9.5 min 60percent MeCNSolvent A WaterSolvent B AcetonitrileSolvent C - Modifier 5percent 4:3:3 880 Ammonia: Acetonitrile: WaterFlow Rate 20 ml/minAt Column Dilution Solvent AcetonitrileAt Column Dilution Flow Rate 1.0 ml/minTransfer solvent 1 ml DMF per tube + MeOH washLCMS 50 mul made upto 1 ml with MeCNAnalytical LCMS Method Phenomenex Gemini 5mu, C18 50 x 2 mm, 1.2 ml/min0 min 95:0:5 A:B:C, 4 min 0:95:5 A:B:CA MeCN, B H2O, C 1:1 MeCN:H2O 1percent Ammonia acid
  • 18
  • [ 39263-32-6 ]
  • [ 628692-15-9 ]
  • [ 944279-14-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 12h; A mixture of Intermediate 3 (602 mg), 2-methoxypyrimidme-5-boronic acid(Frontier, 1.5 eq, 706 mg), and tetrakis(triphenylphosphine)palladium (0) (352 mg) was heated in DME / 2N sodium carbonate (aq, 2:1, 20 ml) at 100 ° for 12 h. Aqueous workup between water and EtOAc gave a brown solid that purified by SPE (Si, 20 g) by elution with DCM (4x10 ml) then EtOAc (4x10 ml), to give a solid that was triturated with DCM / petrol, and filtered to give a light brown solid (660 mg).1H NMR delta 8.85 (2H, s), 7.8 (IH, s), 7.6 (>3H, m), 6.88 (IH, d, J 8.85Hz), 6.3 (2H, s), 3.93 (3H, s); LC-MS rt 2.39 m/z 226 ES-.
  • 19
  • [ 950738-61-1 ]
  • [ 628692-15-9 ]
  • [ 950737-16-3 ]
YieldReaction ConditionsOperation in experiment
10% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 100℃; for 0.277778h;microwave irradiation; To a solution of N-[3-(3-bromo-pyrazolo[1,5-a]pyrimidin-7-yl)-phenyl]-3-trifluoromethyl-benzamide, (100 mg, 0.216 mmol) in ethylene glycol dimethyl ether (3 mL) was added 2-methoxypyrimidine-5-boronic acid (66 mg, 0.433 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (35 mg, 0.043 mmol), sodium carbonate (2M aqueous solution, 0.43 mL, 0.864 mmol). After microwaving at 100° C. for 1000 seconds, the solution was diluted with ethyl acetate, filtered with celite, concentrated, and purified by HPLC (10 mg, 10percent yield). MS 489.2 [M-H]
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