Aniline → Ethyl 4-anilino-2-phenyl-5-pyrimidinecarboxylate

HRID 225335Notes

Reaction equation

HRID 225335 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6115AnilineHCID 239537Ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate

Product 1

HCID 755251Ethyl 4-anilino-2-phenyl-5-pyrimidinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 g. (0.038 mole) of 4-chloro-2-phenyl-5-pyrimidine carboxylic acid ethyl ester and 7.1 g. (0.076 mole) of aniline in 200 ml. of ethanol was refluxed for 3 hours. Upon cooling a yellow solid precipitated from the solution. This was filtered off and rinsed with ethanol to give 4-anilino-2-phenyl-5-pyrimidine carboxylic acid ethyl ester, m.p. 98°-100° C. No further purification was done and the product was used directly in the next step.

Workup

  1. additionA mixture of 10 g
  2. temperatureUpon cooling a yellow solid
  3. customprecipitated from the solution
  4. filtrationThis was filtered off
  5. washrinsed with ethanol

Sources & evidence

ORD record
ord-ad1c193478b04f6694e15f075d97b7b1
Source dataset
uspto-grants-1980_11
Patent number
US04236004

Reaction notes

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