Potassium Hydroxide → Benzyl alcohol, 4-(2,4-diamino-5-pyrimidinylmethyl)-2,6-dimethoxy-alpha,alpha-dimethyl-

HRID 1579319Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C)[C:5]([CH2:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([C:21]([OH:24])([CH3:23])[CH3:22])=[C:15]([O:25][CH3:26])[CH:14]=2)=[CH:4][N:3]=1.[OH-].[K+]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:12][C:13]2[CH:14]=[C:15]([O:25][CH3:26])[C:16]([C:21]([OH:24])([CH3:23])[CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=2)=[CH:4][N:3]=1

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 21568258HCID 21568258, compound

Product 1

HCID 41526Benzyl alcohol, 4-(2,4-diamino-5-pyrimidinylmethyl)-2,6-dimethoxy-alpha,alpha-dimethyl-

Conditions

Temperature: 10 °C

Procedure

A suspension of 11.3 g. of N-{2-amino-5-[4-(1-hydroxy-1-methyl-ethyl)-3,5-dimethoxy-benzyl]-4-pyrimidinyl}-acetamide in 40 ml. of 10% methanolic potassium hydroxide was boiled at reflux for 1 hour and then cooled to about 10°C. The crystals were removed by filtration with suction and washed with a small amount of methanol. After crystallization from methanol, there was obtained 4-[(2,4-diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxy-α,α-dimethyl-benzyl alcohol having a m.p. of 248°-250°C.

Workup

additionA suspension of 11.3 g
temperatureat reflux for 1 hour
customThe crystals were removed by filtration with suction
washwashed with a small amount of methanol
customAfter crystallization from methanol

Sources & evidence

ORD record: ord-c52cbb3ad42e4ad988662bedd88f7ff6
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03931181

Reaction notes

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