9-(3-Benzoyloxypropoxymethyl)guanine → 9-(3-Hydroxypropoxymethyl)guanine

HRID 1577097Notes

Reaction equation

HRID 1577097 reaction equation
C([O:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:20](=[O:24])[NH:19][C:18]([NH2:25])=[N:17][C:16]1=2)(=O)C1C=CC=CC=1>CN>[OH:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:20](=[O:24])[NH:19][C:18]([NH2:25])=[N:17][C:16]1=2

Participants

3

Reactant 1

HCID 1359685319-(3-Benzoyloxypropoxymethyl)guanine

Product 1

HCID 1359234559-(3-Hydroxypropoxymethyl)guanineYield 68.9%

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent

Procedure

A mixture of 9-(3-benzoyloxypropoxymethyl)guanine (0.5 g) and aqueous 45% methylamine (10 ml) was stirred overnight at room temperature. Excess methylamine and water was evaporated at <30° C. under reduced pressure and the residue recrystallized from ethanol to give 9-(3-hydroxypropoxymethyl)guanine (0.24 g), m.p. 223° C. (with resolidification), as the 1/2 hydrate.

Workup

  1. customExcess methylamine and water was evaporated at <30° C. under reduced pressure
  2. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-2e316c98943c447bbfbea5c382adc86f
Source dataset
uspto-grants-1981_09
Patent number
US04287188

Reaction notes

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