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

HRID 2285567Notes

Reaction equation

HRID 2285567 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-91eb330eb0a747dd855ba2850bb25369
Source dataset
uspto-grants-1982_04
Patent number
US04323573

Reaction notes

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