Ethyl orthoformate → [4-(6-Chloro-purin-9-yl)phenyl]-acetic acid ethyl ester

HRID 1661035Notes

Reaction equation

HRID 1661035 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:18]([NH2:19])=[C:17]([Cl:20])[N:16]=[CH:15][N:14]=2)=[CH:8][CH:7]=1)[CH3:2].[CH:22](OCC)(OCC)OCC>>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:22]=[N:19][C:18]3[C:13]2=[N:14][CH:15]=[N:16][C:17]=3[Cl:20])=[CH:10][CH:11]=1)[CH3:2]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 86625828[4-(5-Amino-6-chloro-pyrimidin-4-ylamino)-phenyl]acetic acid ethyl ester

Product 1

HCID 86625827[4-(6-Chloro-purin-9-yl)phenyl]-acetic acid ethyl ester

Procedure

A mixture of [4-(5-amino-6-chloro-pyrimidin-4-ylamino)-phenyl]-acetic acid ethyl ester (0.178 g, 0.58 mmol) and triethyl orthoformate (4 mL, 23.3 mmol, 40 equiv) is stirred for 1 h at reflux. The resulting mixture is allowed to cool to rt and concentrated in vacuo to provide the title compound as a red solid: ES-MS: 317.0 [M+H]+; tR=4.06 min (System 1).

Workup

  1. temperatureat reflux
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bac987689f248e7bb77c96cfacdf63e
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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