Potassium Carbonate → Penciclovir

HRID 2291841Notes

Reaction equation

HRID 2291841 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.C(=O)([O-])[O-:13].[K+].[K+].C([O:25][CH2:26][CH:27]([CH2:37][CH2:38]Br)[CH2:28][O:29]CC1C=CC=CC=1)C1C=CC=CC=1>CN(C)C=O>[OH:25][CH2:26][CH:27]([CH2:28][OH:29])[CH2:37][CH2:38][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:13])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53603492-Amino-6-chloropurineHCID 15928659Benzyl 2-benzyloxymethyl-4-bromobutyl ether

Product 1

HCID 135398748PenciclovirYield 45.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-6-chloropurine (1.275 g, 7.5 mmol) and potassium carbonate (0.69 g, 5 mmol) in dry dimethylformamide (30 ml) was sonicated for 15 min., benzyl 2-benzyloxymethyl-4-bromobutyl ether (1.82 g, 5 mmol) was added, and the mixture was sonicated for 4h and then stirred over-night. After evaporation in vacuum the residue was extracted with 3×50 ml of chloroform and the extracts were evaporated to dryness in vacuum. Chromatography (silica gel, chloroform+methanol 20+1 by volume) afforded 0.58 g (26%) of pure compound 4-(2-amino-6-chloropurin-9-yl)-2-benzyloxymethylbutyl benzyl ether. A small sample of said compound was recrystallized from toluene. M.p. 108.5°-109.5° C.

Workup

  1. customwas sonicated for 15 min.
  2. customAfter evaporation in vacuum the residue
  3. extractionwas extracted with 3×50 ml of chloroform
  4. customthe extracts were evaporated to dryness in vacuum

Sources & evidence

ORD record
ord-3dc422ea8cbe4043806048a45cae7bf7
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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