Ethyl orthoformate → Ethyl 1-(4-Chlorophenyl)-1,6-dihydro-2,4-dimethyl-6-oxopyrimidine-5-carboxylate

HRID 25868

Reaction equation

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

Participants

Reactant 3

HCID 31214Ethyl orthoformate

HCID 66221Triethyl orthoacetate

HCID 70610046Ethyl 3-amino-2-(4-chlorophenylcarbamoyl)crotonate

Product 1

HCID 21325489Ethyl 1-(4-Chlorophenyl)-1,6-dihydro-2,4-dimethyl-6-oxopyrimidine-5-carboxylateYield 42%

Procedure

This compound is prepared in 42% yield from ethyl 3-amino-2-(4-chlorophenylcarbamoyl)crotonate in a manner analogous to Example 1 substituting triethyl orthoacetate for triethyl orthoformate.

Sources & evidence

ORD record: ord-507868586bd341fa949a7da51d5fcec3
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04147528

Linked notes

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