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CAS No. :104227-87-4 MDL No. :MFCD00866964
Formula : C14H19N5O4 Boiling Point : -
Linear Structure Formula :N4C5H2(NH2)CH2CH2CH(CH2OCOCH3)2 InChI Key :GGXKWVWZWMLJEH-UHFFFAOYSA-N
M.W : 321.33 Pubchem ID :3324
Synonyms :
BRL 42810
Chemical Name :2-(2-(2-Amino-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate

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Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
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Application In Synthesis of [ 104227-87-4 ]

* 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 [ 104227-87-4 ]

[ 104227-87-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 97845-60-8 ]
  • [ 104227-87-4 ]
YieldReaction ConditionsOperation in experiment
90.9% With water; ammonium formate;palladium on charcoal; In ethyl acetate; for 2h;Product distribution / selectivity; Into a jacketed reactor equipment with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added wet 10 % PD/C (4 g, 50 % HA0), EtOAc (220 ml), C1-FMC (20 g; 56.1 mmol) and ammonium formate (4.37 G ; 67.28 mmol ; 20 % excess). The reaction was completed after 2 hours, as all the CL-FMC was consumed. The reaction mixture was filtered at 50C and the filtrate was evaporated to dryness, leaving 16.4 g of solid (90.9 % of the 18 g expected).
90% With ammonium formate;palladium; In methanol; water; Example 2 9-(4-Acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine A suspension of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine (0.36g, 1.0mmol) and 10% palladium-on-charcoal (30mg) in methanol containing ammonium formate (400mM , 10ml) was heated under reflux for 30 minutes. The mixture was allowed to cool, filtered and the solvent removed. The residue was taken up in water and the solution extracted twice with chloroform. The organic layers were combined, dried (magnesium sulphate) and the solvent removed to afford 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine (0.29g, 90%). Recrystallisation from ethyl acetate-hexane gave white shiny plates (0.25g, 78%) m.p. 102-104C; λmax (MeOH) 222 (27,500), 244 (4,890), and 309 (7,160)nm; νmax (KBr) 3340, 3170, 1745, 1730, 1660, 1615 and 1580cmmin1; δH(CDCl3) 1.90-2.05 (3H, m, 2'-H and 3'-H), 2.07 (6H, s, 2 x CH3), 4.15 (4H, d, J 5.2 Hz, 2x4'-H), 4.21 (2H, t, J 7.2Hz, 1'-H), 5.16 (2H, br s, 2-NH2), 7.79 (1H, s, 8-H), and 8.70 (1H, s, 6-H); (Found: C, 52.10; H, 6.00; N, 21.49%. C14H19N5O4 requires C, 52.33; H, 5.96; N, 21.79%).
90% With ammonium formate;palladium 10% on activated carbon; In methanol; for 2h;Heating / reflux; A mixture of 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloro-purine (28.1 mmoles, 10 g), prepared according to Example 3 or 4, 10% palladium on charcoal (0.833 g) and ammonium formate (4 eq/mole, 7.08 g) in methanol (270 ml) is refluxed for 2 h under stirring. The mixture is cooled to room temperature and filtered and the filtrate is evaporated under reduced pressure to give a thick, colourless oil. The residue is then taken up into water (150 ml) and extracted with chloroform (2x100 ml). The combined organic phases are dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude is purified by crystallization from ethyl acetate/hexane to afford 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-aminopurine (8.19 g) in a 90% yield.1H-NMR (CDC13) (d, ppm): 1.87-1.95 (m, 3H, CH and CH2) 2.00 (s, 6H, 2xCH3) 4.07 (d, 4H, 2xCH2O) 4.18 (t, 2H, CH2N) 5.17 (br, 2H, NH2) 7.72 (s, 1H, CH) 8.63 (s, 1H, CH).13C-NMR (CDC13) (d, ppm): 20.82 (2xCH3) 28.83 (CH2) 34.95 (CH) 40.79 (CH2N) 63.65 (2xOCH2) 128.21 () 142.16 (C) 149.90 (CH) 153.20 (C) 159.95 (C) 170.70 (2xCO). EI-MS: 321 m/z (M+).
75% With ammonium formate;palladium on charcoal; In ethyl acetate; at 70℃; for 5h;Product distribution / selectivity; Cl-FMC (145 g), 10 % PD/C (28. 92 g), and ammonium formate (31.7 g) were dissolved in EtOAc (1,450 ml) at 70C. After 5 hours hot filtration was performed, the solution was concentrated by distillation of EtOAc (vacuum, 41C). After complete dissolution of the precipitated solid at 60C, the solution was cooled for 1 hour to 5C and left overnight before separating the resulting product. Reaction yield-75 % (based on Cl- FMC).
With ammonium formate;50% Pd/C; In methanol; at 5 - 50℃; for 3h; Example 2; 47 g of compound of formula (II) and 2.4 g of 10% palladium on charcoal (50% wet) are added under nitrogen to 240 ml of methanol. The mixture is cooled to 5-10C and then 32 g of ammonium formate are added. The reaction mixture is heated at 50C for 3 hours. After cooling and filtering the black solid, the filtrate is evaporate to dryness. The residue is partitioned in methylene chloride and water. The organic phase is separated from the aqueous phase and concentrated in vacuo. The residue is dissolved in 130 ml of ethyl acetate. 0.5 g of charcoal and 1.0 g of diatomaceous earth are added to this solution, which is refluxed for half an hour. The mixture is then filtered and the filtrate is allowed to crystallize at 15-20C. The obtained crystals are filtered and washed with 2x25 ml of cold ethyl acetate. After drying at 50C in a drying oven until constant weight, 33 g of almost pure (HPLC purity >99%) Famciclovir (I) are obtained.
With palladium on activated charcoal; ammonium formate; In methanol; acetic acid; at 60℃; for 1.5h; Add 500ml of methanol to the reaction flask, add 18g of 2-[2-(6-chloro-2-amino-9H-purin-9-yl)ethyl]-1,3-propanediol-diacetate (G4) under stirring , Ammonium formate 22.5g, Acetic acid 10ml, Add palladium on carbon Kg, Stir and heat to 60 to start timing reaction, Take an appropriate amount of the reaction solution at 5, 15, 25, 35, 45, 60, and 90 minutes, respectively. The reaction liquid is filtered to remove the catalyst palladium carbon and then diluted,

  • 2
  • [ 97845-60-8 ]
  • [ 104227-87-4 ]
  • [ 104227-86-3 ]
  • [ 120687-07-2 ]
YieldReaction ConditionsOperation in experiment
64% With ammonium formate;palladium on charcoal; In methanol; acetic acid methyl ester; at 40℃; for 6.16667h;Product distribution / selectivity; Into a jacketed reactor equipped with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added dry 7 % Pd/C (3.48 g), MeOAc (500 ml), MEOH (50 ml), Cl-FMC (50.1 g; 49.6 mmol), and ammonium formate (27. 18 g; 97 % pure). The reaction mixture was heated at 40C for 6 hours and 10 min. At this stage 98. 37 % FMC, 0.82 % MH-FMC and 0.63 % DH-FMC and 0.18 % Cl- FMC; were detected. Upon cooling the reaction mixture and filtering the black solid, the filtrate was evaporated to dryness leaving 43.77 g solid (almost the entire expected amount of FMC; assay 97.3 % FMC). The composition of the solid was left unchanged from the above quotation. The solid was partitioned in EtOAc (365 ml) and water (150 ml). The organic phase was washed with H20 (45 ml), and kept aside. The combined aqueous phases were washed with EtOAc (3 x 40 ml). The combined EtOAc extracts were washed with H20 (40 ml), and kept aside. The aqueous phases were extracted again with EtOAc (2 x 40 ml). The EtOAc extracts were washed with HA0 (10 ml), and kept aside. The three organic phases were combined, dried with MGS04 and evaporated to dryness leaving 34.7 g white solid (-76. 8 % yield). The solid was crystallized in BUOH (100 ml; 63C) giving 28.9 g pure FMC (64 % yield). Less then 0.1 % impurities (each) were detected in the crystals.
With ammonium formate;palladium on charcoal; In methanol; acetic acid methyl ester; at 40℃; for 1.6 - 6h;Product distribution / selectivity; Into a jacketed reactor equipped with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added dry 11.4 % PD/C (2.3 G), MeOAc (200 ml), MEOH (20 ml), CL-FMC (20 g; 55. 8 mmol), and ammonium formate (10.5 g; 97 % pure). The reaction mixture was heated at 40C. Complete conversion of CL-FMC was observed within 1 hr and 40 min. Under these conditions two hydrolysis by-products, mono-hydroxy FMC (MH-FMC) and di-hydroxy FMC (DH-FMC) were formed, 0.9 % and 0.64 %, respectively. The reaction mixture was left to stir for a total of 4 hours at 40C. This did not have a significant effect on the level of the by-products THAT REMAINED STEADY, I. E. , THE MH-FMC AND DH-FMC LEVEL WAS 1. 05 % AND 0. 72 %, respectively. The reaction was cooled to room temperature, then filtered. This solid retained 0.9 % MH-FMC and only 0.6 % of the DH-FMC.; Example 3 Preparation of Acetic acid 2-acetoxymethyl-4- (2-amino-purin-9-yl)-butyl ester (FMC) from Acetic acid 2-acetoxymethyl-4- (5-amino-7-chloro-imidazo [4,5- B] PYRIDIN-3-YL) -BUTYL ESTER (CL-FMC) Into a jacketed reactor equipped with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added dry 5.38 % Pd/C (1.07 g), MeOAc (200 ml), MEOH (20 ml), Cl-FMC (20.04 g; 55.85 mmol), and ammonium formate (10.48 g; 97 % pure). The reaction mixture was heated at 40C for 6 hours. The reaction mixture composition was 96.7 % FMC, 0.86 % DH-FMC, 1.07 % of MH-FMC and 1.27 % Cl-FMC. The reaction mixture was cooled to room temperature, filtered and the filtrate was evaporated to dryness leaving 17.94 g of white solid (assay 94.8 % FMC).
With water; ammonium formate;palladium on charcoal; In methanol; acetic acid methyl ester; at 40℃; for 4h;Product distribution / selectivity; Into a jacketed reactor equipped with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added wet 5.7 % Pd/C (2.27 g; 50% H20), MeOAc (110 ml), MEOH (110 ml), CL-FMC (20 g; 55.74 mmol), and ammonium formate (10.54 g; 97% pure). The reaction mixture was heated at 40C for 4 hours. The reaction mixture composition was 96.3 % FMC, 1.06 % DH-FMC, 2.64 % OF MH-FMC. No Cl-FMC was detected. The reaction mixture was cooled, filtered. The filtrate was concentrated to 53.5 g slurry. The white solid was filtered and washed with hexane, leaving 19.24 g solid (assay 87.5% FMC; expected amount 17.91g).
With water; ammonium formate;palladium on charcoal; In acetic acid methyl ester; at 40℃; for 4.5h;Product distribution / selectivity; Into a jacketed reactor equipped with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added 5.46 % Pd/C wet (2.27 g; 50 % H20), MeOAc (220 ml), CL-FMC (21 g; 58. 5 mmol), and ammonium formate (10.66 g; 97 % pure). The reaction mixture was heated at 40C for 4.5 hours. The reaction mixture composition was 74.47 % FMC, 0.64 % DH-FMC, 0.74 % of MH-FMC and 35 % Cl- FMC. MEOH was added (20 ml) and the reaction mixture was left for 1 more hour at 40C, then cooled to room temperature and stirred overnight. The reaction proceeded further and the composition of the reaction mixture was 89. 6 % FMC, 0.73 % DH-FMC, 0.9 % of MH-FMC and 8.8 % Cl-FMC. Heating was continued 135 min. more at 40C and the composition of the reaction mixture was 93.05 % FMC, 0.81 % DH-FMC, 1 % of MH-FMC and 5 % Cl-FMC. The reaction mixture was filtered and the filtrate was concentrated to 40.3 g of slurry. The solid was filtered and washed to give 13.64 g solid composed of 97.53 % FMC, 0.34 % DH-FMC, 0.69 % OF MH-FMC and 1.44 % CL-FMC (assay 96.5% FMC).
With water; ammonium formate;palladium on charcoal; In methanol; at 40℃; for 4.5h;Product distribution / selectivity; Into a jacketed reactor equipped with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added wet 5.56 % Pd/C (4.4 g; 50% H20), MEOH (440 ml), Cl-FMC (40 g; 111.5 mmol), and ammonium formate (21.96 g; 97 % pure). The reaction mixture was heated at 40C for 4.5 % hours. The reaction mixture composition was 95.8 % FMC, 0.55 % DH-FMC, 3.3 % of MH-FMC. No Cl- FMC was detected. The reaction mixture was cooled and filtered.
With ammonium formate;palladium on charcoal; In methanol; ethyl acetate; at 40℃; for 5.16667h;Product distribution / selectivity; Into a jacketed reactor equipped with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added dry 5.4 % PD/C (1.07 g), EtOAc (220 ml), MEOH (20 ml); Cl-FMC (20 g; 55.8 mmol), and ammonium formate (10.5 g; 97 % pure). The reaction mixture was heated at 40C for 5 hours 10 min. The reaction mixture composition was 50.57 % FMC, 0.54 % DH-FMC, 0.53 % OF MH-FMC and 48.36 % Cl-FMC. MEOH was added (20 ml) and the reaction mixture continued at 40C for 80 min. more. Leaving the composition unchanged. The reaction mixture was left to stir overnight at room temperature. While the CL-FMC was consumed slightly more (44.1 %) the MH-FMC and DH-FMC level remained steady. After heating to 40C 3 hours more showed a progress of the reaction to 76.7 % FMC, 0.67 % DH-FMC, 0.93 % MH-FMC and 21.53 % Cl-FMC. More MEOH was added (40 ml) and the reaction was continued 2.5 hours. The composition of the reaction mixture was 96.14 % FMC, 0.79 % DH-FMC, 1.3 % of MH-FMC and 1.55 % Cl-FMC. After cooling to room temperature, the reaction mixture was filtered and the filtrate was evaporated to dryness leaving 17.45 g solid composed of 97. 48 % FMC, 0.64 % DH-FMC, 1.14 % OF MH-FMC and 0.72 % CL-FMC (assay 97.1 % FMC).

  • 3
  • [ 97845-60-8 ]
  • [ 104227-87-4 ]
  • [ 120687-07-2 ]
YieldReaction ConditionsOperation in experiment
89.7% With water; ammonium formate;palladium on charcoal; In ethyl acetate; at 50℃; for 5h;Product distribution / selectivity; Into a jacketed reactor equipped with a mechanical stirrer, a reflux condenser and a thermocouple, under an inert atmosphere (N2), was added wet 10 % Pd/C (12 g, 50 % H20), EtOAc (660 ml), CL-FMC (60 g; 168.6 mmol), and ammonium formate (32.8 g; 504.5 mmol; 97 % pure). The reaction mixture was heated at 50C. After 5 hours, all the CL-FMC was consumed, and the composition of the reaction mixture showed 99.6 % FMC, 0. 1 %, of MH-FMC and traces of the DH-FMC. The reaction mixture was filtered at 50C and the filtrate was evaporated to dryness, leaving 51.5 g of solid (95 % of the 54.2 g expected). The solid was crystallized from n-BuOH (61C ; 155 ml). After cooling in ice-water bath, filtration and drying (6 hrs ; 60C) 48.6 g of pure FMC (89.7 % yield) was obtained (99.8 % FMC; MH-FMC level was less than 0.1 % HPLC area %).
62 - 69.8% With water; ammonium formate;palladium on charcoal; In ethyl acetate; at 50 - 70℃; for 4 - 5h;Product distribution / selectivity; Into a jacketed reactor equipped with a mechanical stirrer and a reflux condenser, under an inert atmosphere (N2), was added wet 10 % Pd/C (18.9 g, 52 % H20), EtOAc (423 ml) AND CL-FMC (90 g; 252.9 mmol). The reaction mixture was heated to 70C. Ammonium formate (19.7 g; 312.4 mmol) was added in 11 portions. The portions were added every 20 min. After 4 hours, all the Cl-FMC was consumed. The reaction mixture was diluted to 720 ml and filtered at 40C. A charcoal (4.5 g) was added to the filtrate and the mixture was stirred for 30 min. Then the charcoal was filtered out and washed (90 ml) EtOAc. The wash was added to the filtrate. The filtrate was distillated back to 423 ml of EtOAc. Precipitation occurred during the distillation. The mixture was heated until a clear solution was obtained. Then the solution was cooled (4 hrs; 10C) and precipitation occurred during the cooling process. After 12 hrs of stirring, the material was filtered out and was washed with water, and a wet famciclovir was obtained. The material was dried 3 hr at 45C and 3 hr at 65C. FMC (62 % yield) was obtained (MH- FMC level was 0.03 % HPLC).Example 13 Preparation of Acetic ACID ? 2-ACETOXYMETHYL-4-(2-AMINO-PURIN-9-YL)-BUTYL ester (FMC) from Acetic acid 2-acetoxymethyl-4- (5-amino-7-chloro-imidazo [4,5- B] PYRIDIN-3-YL)-BUTYL ester (Cl-FMC) Into a jacketed reactor equipped with a mechanical stirrer and a reflux condenser, under an inert atmosphere (N2), was added wet 10 % PD/C (68. 7 g, 52 % H20), EtOAc (1550 ml) and Cl-FMC (330 g ; 927. 5 MMOL). The reaction mixture was heated to 50C. Ammonium formate (71.2 g; 1130.3 mmol) was added in 11 portions. The portions were added every 20 min. After 5 hours, all the Cl-FMC was consumed. The reaction mixture was diluted to 2640 ml and filtered at 50C. A charcoal (16.5 g) was added to the filtrate and the mixture was stirred for 30 min. Then the charcoal was filtered out and washed (330 ML) OF ETOAC. The wash was added to the filtrate. The filtrate was DISTILLATED back TO 1, 550 ML OF EOTAC. The mixture was heated until a clear solution obtained. Then the solution was cooled (5.5 hrs ;-10C) and precipitation occurred during the cooling process. After 12 hr of stirring, the material was filtered out and was washed with water, and a wet famciclovir was obtained. The material was dried 3 hr at 45C and 3 hr at 65C. FMC (69.8 % yield) was obtained (MH-FMC level was 0.06 % HPLC).
0.27 - 0.29%Chromat. A MIXTURE OF 6. 2 G wet "10 % Pd/C"(wt Pd/wt Pd+C) 52.14 % H2O (wt H2O/wt of Pd+C+H2O), H2O (120 ml) and Cl-FMC (30 g; 83.1 mmol) was added, under an inert atmosphere of nitrogen, into a JACKETED REACTOR EQUIPMENT with a mechanical stirrer, a reflux condenser and a THERMOCOUPLE. THE MIXTURE WAS HEATED TO 42C. A solution of ammonium FBNNATE (6. 5 g; 99.7 MMOL; 20 % excess) in 20 ml H20 was added dropwise for 2. 5 HOURS. AFTER 30 min., charcoal (3 G) was added and the solution was continued to be stirred for an additional time of 30 min. The reaction mixture was filtered, and the catalyst was washed with 10 ml H2O. The filtrate was stirred for 2 hours in an ice bath (2C). The precipitated solid was filtered and washed WITH 15 ML cold 20, LEAVING 31. 5 g wet solid precipitate. Upon drying, 22. 4 G of a very white solid was obtained (83. 6% of the expected). The MH-FMC LEVEL WAS 0. 29% and the FMC yield was 83.3 % (HPLC area %). Example 2 Preparation of Acetic acid 2-acetoxymethyl-4-(2-amino-purin-9-yl)-butyl ester (FMC) from 9-[4-acetoxy-3(acetoxymethyl)but-1-yl]-2-amino-6-chloropurine-(Cl- FMC) A MIXTURE OF 6. 2 G WET"10% PD/C" (BASED on the weight of Pd+C) with 52. 14 % H2O (wt H2O/wt of Pd+C+H2O), H2O (120 ml) and Cl-FMC (30 g; 83.1 MMOL) WAS ADDED,-UNDER AN INERT ATMOSPHERE OF NITROGEN, INTO a JACKETED REACTOR equipment with a MECHANICAL STIRRER, a reflux condenser and a thermocouple. The mixture was preheated to 35C. A solution of ammonium formte (5.4 g; 83.1 mmole; 8.4% in excess) in 20 ml H2O was added dropwise for 2.5 hours. After 30 MIN., CHARCOAL (3 G) WAS ADDED AND the solution was stirred for 30 min. The reaction mixture was filtered, and the catalyst obtained was washed with 10 ml H2O. The filtrate was stirred for 2 hours in an ice bath (2C). The precipitated solid was filtered and washed with 15 ml cold H2O, leaving 31.5 g wet solid precipitate. Upon drying, 22. 4 g of a very white solid was obtained (81.3% OF THE EXPECTED). THE MH-FMC level was 0.27% and the CL-FMC was 0. 08% (HPLC area %). All other impurities levels were less than 0. 06% (HPLC AREA %). Example 3 PREPARATION OF ACETIC ACID 2-ACETOXYMETHYL-4- (2-AMINO-PUNN-9-YL)-BUTYL ESTER (FOC) FROM 9- [4-ACETOXY-3- (ACETOXYMETHYL) BUT-L-YL]-2-AMINO-6-CHLOROPUNNE (CL- FMC) Into A JACKETED REACTOR EQUIPMENT with a mechanical STIRRER, a reflux condenser and a thermocouple, under an inert atmosphere (N2), a mixture of wet"10 % P LIJC (D 2 g, wherein the 10% is based on THE COMBINED WEIGHT OFPD AND C, HAVING 52. 14 % I20 (WT OF NZO/WT OF P+C+H2C3)),,-HSO (120 ML) and C1-FMC (30 G ; 83. 1 MMO .) was added. The mixture was maintained at room temperature. A solution of ammonium formate (5.4 g; 83. 1 mmole ; 8.4% in excess) in 20 ML H20 was added DROPWISE FOR 6 HOURS. AFTER 30 MIN. , CHARCOAL (3 G) WAS ADDED AND THE SOLUTION WAS stirred for 30 min. The reaction mixture was filtered, and the catalyst was washed with 10 ml H20. The filtrate was stirred for 2 hours in an ice bath (2C). The precipitated solid was filtered and washed with 15 ml cold H20, leaving 31.5 g wet solid precipitate. Upon drying, 22.4 g of a very white solid was obtained (81.3% of the expected). The MH-FMC level was 0.27% and the CL-FMC was 0. 08% (HPLC area %). All other impurities were less than 0. 06% (HPLC area %).
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