Formic Acid → 2-[(2-Amino-6-oxo-3,6-dihydro-9H-purin-9-yl)methoxy]ethyl formate

HRID 614946Notes

Reaction equation

HRID 614946 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.[CH:17](O)=[O:18]>CCOCC>[CH:17]([O:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2)=[O:18]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 135398513Acyclovir

Product 1

HCID 1361209032-[(2-Amino-6-oxo-3,6-dihydro-9H-purin-9-yl)methoxy]ethyl formate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 9-(2-hydroxyethoxymethyl)guanine (4.73 g) in 97% formic acid (24 ml) was stirred at room temperature overnight. The amber solution was diluted with about 200 ml of dry ether and chilled. The resulting white precipitate was filtered, dried and recrystallized from dry dimethylformamide to give 9-(2-formyloxyethoxymethyl)guanine (3.6 g, m.p. 225°-227° C.).

Workup

  1. temperaturechilled
  2. filtrationThe resulting white precipitate was filtered
  3. customdried
  4. customrecrystallized from dry dimethylformamide

Sources & evidence

ORD record
ord-12fee3e78fd044f9be67b9dc613390a9
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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