Pyridine → 4-Acetoxy-3-(acetoxymethyl)but-1-yl-2-aminopurine

HRID 273281

Reaction equation

HRID 273281 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=CN2CCC(CO)CO)=[CH:4][N:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:24]([O:27][C:28](=[O:30])[CH3:29])(=O)C>O1CCCC1.CN(C)C1C=CN=CC=1>[C:28]([O:30][C:9]12[N:18]=[C:23]([CH2:22][CH2:21][CH:20]([CH2:24][O:27][C:28](=[O:30])[CH3:29])[CH3:19])[N:6]=[C:5]1[CH:4]=[N:3][C:2]([NH2:1])=[N:10]2)(=[O:27])[CH3:29]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1285176-Deoxypenciclovir

Product 1

HCID 866091624-Acetoxy-3-(acetoxymethyl)but-1-yl-2-aminopurineYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

23.73 g (0.1 mole) of 2-amino-9-(4-hydroxy-3-(hydroxymethyl)but-1-yl)purine was suspended in 300 ml of tetrahydrofuran. To the suspension, 24.52 g (0.31 mole) of pyridine, 1.22 g (0.01 mole) of 4-dimethylaminopyridine and 21.44 g (0.21 mole) of acetic acid anhydride were added, and the mixture was stirred for five hours at room temperature. After completion of the reaction, the reaction product was concentrated under reduced pressure. The remaining concentrate was added to 300 ml of purified water and then extracted four times with 400 ml portions of chloroform. The organic layer was collected, and dried with anhydrous magnesium sulfate, followed by filtration and washing. The resulting filtrate was concentrated under reduced pressure and crystallized from butanol, thereby giving 24.10 g (75% yield) of white 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl-2-aminopurine (famciclovir).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction product was concentrated under reduced pressure
  3. concentrationThe remaining concentrate
  4. additionwas added to 300 ml of purified water
  5. extractionextracted four times with 400 ml portions of chloroform
  6. customThe organic layer was collected
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfollowed by filtration
  9. washwashing
  10. concentrationThe resulting filtrate was concentrated under reduced pressure
  11. customcrystallized from butanol

Sources & evidence

ORD record
ord-ba39120c9555468b906f45ef3bc6df9b
Source dataset
uspto-grants-2008_11
Patent number
US07456282B2

Linked notes

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