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

HRID 2050029Notes

Reaction equation

HRID 2050029 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 precipitation 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. customThe resulting white precipitation
  3. filtrationwas filtered
  4. customdried
  5. customrecrystallized from dry dimethylformamide

Sources & evidence

ORD record
ord-41defff4d2024b6aa349cdeabe9992e0
Source dataset
uspto-grants-1980_04
Patent number
US04199574

Reaction notes

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