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[ CAS No. 97845-60-8 ] {[proInfo.proName]}

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Product Details of [ 97845-60-8 ]

CAS No. :97845-60-8 MDL No. :MFCD08458206
Formula : C14H18ClN5O4 Boiling Point : -
Linear Structure Formula :- InChI Key :KXPSHSVVYGZKAV-UHFFFAOYSA-N
M.W : 355.78 Pubchem ID :10155164
Synonyms :
Chemical Name :2-(2-(2-Amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate

Safety of [ 97845-60-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338-P304+P340 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 97845-60-8 ]

* 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 [ 97845-60-8 ]

[ 97845-60-8 ] Synthesis Path-Downstream   1~10

  • 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
  • [ 127047-77-2 ]
  • [ 10310-21-1 ]
  • [ 97845-60-8 ]
  • [ 97845-61-9 ]
YieldReaction ConditionsOperation in experiment
56%; 7% With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 18h; A mixture of 2-amino-6-chloropurine (58.9 mmoles, 10 g) and anhydrous potassium carbonate (1.5 eq/mole, 12.22 g) in anhydrous dimethylformamide (240 ml) is added with 2-acetoxymethyl-4-iodo-butyl-1-acetate (58.9 mmol, 18.49 g), prepared according to Example 2. The mixture is stirred at room temperature for 18 h, then water is added (150 ml) and the products are extracted with dichloromethane (3x100 ml). The combined organic phases are washed with a sodium chloride saturated solution (3x100 ml), dried over anhydrous sodium sulfate and then evaporated under reduced pressure. The residue is fractioned by column chromatography (eluent dichloromethane/methanol 97/3) to give two white solids: 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloropurine (11.7 g) and 7-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloropurine (1.46 g) in yields of 56% and 7%, respectively.9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloropurine: 1H-NMR (CDC13) (d, ppm): 1.80-2.05 (m, 3H, CH and CH2) 2.02 (s, 6H, 2xCH3) 4.08 (d, 4H, 2xCH2O) 4.16 (t, 2H, CH2N) 5.32 (br, 2H, NH2) 7.76 (s, 1H, CH).13C-NMR (CDC13) (d, ppm): 21.43 (2xCH3) 29.44 (CH2) 35.54 (CH) 41.95 (CH2N) 64.22 (2xOCH2) 123.43 (C) 142.66 (C) 151.95 (CH) 154.02 (C) 159.78 (C) 171.47 (2xCO). EI-MS: 355 m/z (M+).7-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloropurine: 1H-NMR (CDC13) (d, ppm): 1.88-2.03 (m, 3H, CH and CH2) 2.02 (s, 6H, 2xCH3) 4.09 (d, 4H, 2xCH2O) 4.41 (t, 2H, CH2N) 5.28 (br, 2H, NH2) 7.99 (s, 1H, CH).13C-NMR (CDC13) (d, ppm): 20.76 (2xCH3) 30.76 (CH2) 35.26 (CH) 44.98 (CH2N) 63.62 (2xOCH2) 114.45 (C) 142.06 (C) 148.38 (C) 159.43 (CH) 164.46 (C) 171.47 (2xCO). EI-MS: 355 m/z (M+).
  • 3
  • [ 108-24-7 ]
  • [ 172529-94-1 ]
  • [ 97845-60-8 ]
YieldReaction ConditionsOperation in experiment
80.8% With dmap; triethylamine; In dichloromethane; at 20℃; Dichloromethane 125ml (1.94mol), 2-amino-6-chloro-9-(3-hydroxymethyl-4-hydroxy-1-butyl)purine 15g (0.055mol), 4-dimethylaminopyridine 0.16g (0.001mol), 7.65g (0.076mol) of triethylamine was put into the reaction bottle and stirred, 23.4 g (0.23 mol) of acetic anhydride was added dropwise at RT. After the addition was complete, the reaction was incubated until TLC (dichloromethane: methanol = 10: 1 (V / V)) showed that the reaction was complete. Cool to 20 C and adjust the pH to 6.0-7.0 with 25% aqueous sodium hydroxide solution. After standing for separation, the organic layer was distilled under reduced pressure to near dryness, 40 ml of methanol / water (V / V = 3/1) was added, heated to full solution, slowly cooled to 4 C, and stirred for 1 h. Filtration and vacuum drying at 45-60 C gave 15.83 g of 2-amino-6-chloro-9-(3-acetoxymethyl-4-acetoxy-1-butyl)purine in 80.8% yield.
  • 4
  • [ 97845-60-8 ]
  • [ 39809-25-1 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogenchloride; In water; for 3h;Reflux; Industrial scale; Weigh compound II (978.40g, 2.75mol) and add it to 8.25L hydrochloric acid (2mol/L), and react under reflux for 3 hours. Cool to room temperature, add NaOH solution (14mol/L),Adjust the pH to 14.0. Wash with ethyl acetate,Add hydrochloric acid (6mol/L) to the water phase,Adjust the pH to neutral, and a large number of white crystals will be precipitated. After filtering, washing and drying, 675.57 g of penciclovir was obtained with a yield of 97.0%.The chemical purity is 99.99%.
91.5% With formic acid; In water;Reflux; Purified water 88ml (0.055ml), formic acid 12g (0.26mol), 2-amino-6-chloro-9-(3-acetoxymethyl-4-acetoxy-1-butyl)purine 15.83g ( 0.044mol) into the reaction bottle, stir and heat to reflux for 5-7h. Cool, add 25% aqueous sodium hydroxide solution at RT to adjust the pH to 6.5-7.5, precipitate solids, cool to 15 C, filter, and wash the filter cake with purified water. Vacuum drying at 50 C. gave 10.31 g of penciclovir in 91.5% yield.
85% In hydrogenchloride; Alternative procedure for preparation of 9-(4-Hydroxy-3-hydroxymethylbut-1-yl)guanine (Example 4) A solution of 9-(4-acetoxy-3-acetoxymethyl-but-1-yl)-2-amino-6-chloropurine (15.5g, 43.6mmol) in 2M hydrochloric acid (150ml) was heated under reflux for 2 hours. The solution was then cooled to room temperature and neutralised with 10% sodium hydroxide solution, left to stand at 4oC, and the resulting precipitate filtered off, washed with cold water and recrystallized from water to give 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine as a white crystalline solid (9.4g, 85%) mp 275-277o.
  • 5
  • [ 128139-38-8 ]
  • [ 10310-21-1 ]
  • [ 97845-60-8 ]
  • [ 97845-61-9 ]
  • 6
  • acetic acid 2-acetoxymethyl-4-(2-acetylamino-6-chloro-purin-9-yl)-butyl ester [ No CAS ]
  • [ 97845-60-8 ]
  • 9
  • [ 128139-38-8 ]
  • [ 10310-21-1 ]
  • [ 97845-60-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetraethylammonium bromide; In N,N-dimethyl-formamide; at 60 - 70℃; for 6h; Example 1; 70.2 ml of triethylamine are added to a stirred solution of 2-acetoxymethyl-4-hydroxybutyl acetate (63.9 g) in toluene; during the addition the temperature is kept at 0C. The reaction mixture is then cooled to -10C and 29.5 ml of methanesulphonyl chloride are added drop by drop while keeping the temperature below 0C. After completion of the addition, the reaction mixture is stirred for a further 1.5 hour, then washed with 350 ml of water and subsequently with 7.02 ml of concentrated HCl. The organic phase is separated from the aqueous phase, which is back-extracted with 140 ml of toluene. The organic fractions are pooled and washed with 170 ml of water. The organic phase is separated and concentrated in vacuo. 60 ml of DMF are added and the organic phase is concentrated in vacuo again. Finally 600 ml of DMF are added followed by 53.7 g of anhydrous potassium carbonate, 45 g of 6-chloroguanine and 6.5 g of tetraethylammonium bromide. The reaction mixture is stirred for 6 hours at 60-70C and then is allowed to cool to room temperature. Insoluble materials are filtered off and 810 ml of water are then added to the filtrate, which cause immediate formation of a white precipitate. The slurry is then stirred at 15C for about one hour. The solid is collected by filtration, washed with water and then dissolved in 365 ml of hot methanol. 1.2 g of charcoal and 2.5 g of diatomaceous earth are added to this solution, which is refluxed for half an hour and then filtered; the filtrate is concentrated in vacuo to approximately 250 ml and is finally allowed to crystallize at 10C. The resulting crystals are filtered and washed with 50 ml of cold methanol. After drying at 45C in a drying oven until constant weight, 59.5 g of almost pure (HPLC purity >99%) derivative of formula (II) are obtained.
  • 10
  • [ 97845-60-8 ]
  • 2-amino-6-dimethylamino-9-(4-hydroxy-3-hydroxy-methylbutyl)purine [ No CAS ]
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