Aniline → Ethyl 2-anilino-1,6-dihydro-6-oxo-5-pyrimidinecarboxylate

HRID 979136Notes

Reaction equation

HRID 979136 reaction equation
CS[C:3]1[NH:4][C:5](=[O:14])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:8]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[NH:15]([C:3]1[NH:4][C:5](=[O:14])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:8]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 239049Ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylate

Product 1

HCID 13913527Ethyl 2-anilino-1,6-dihydro-6-oxo-5-pyrimidinecarboxylateYield 61.2%

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate (5 g) and aniline (2.6 g) is heated without solvent at 130° C. for 1 hour. After cooling, the resulting solid is pulverized and recrystallized from DMSO to give ethyl 2-anilino-1,6-dihydro-6-oxo-5-pyrimidinecarboxylate (3.7 g). M.p. 267°-269° C.

Workup

  1. temperatureAfter cooling
  2. customrecrystallized from DMSO

Sources & evidence

ORD record
ord-423ed751c0014bc68a7e97ed611f9e6c
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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