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

HRID 848099Notes

Reaction equation

HRID 848099 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-22fb52c1062f40b9968b5a4b0584da80
Source dataset
uspto-grants-1981_10
Patent number
US04294831

Reaction notes

Loading…