Allylamine → Ethyl 4-(allylamino)-2-phenyl-5-pyrimidinecarboxylate

HRID 127376

Reaction equation

HRID 127376 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].[CH2:19]([NH2:22])[CH:20]=[CH2:21]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:22][CH2:19][CH:20]=[CH2:21])=[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 7853AllylamineHCID 239537Ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate

Product 1

HCID 2767635Ethyl 4-(allylamino)-2-phenyl-5-pyrimidinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5 g. (0.019 mole) of 4-chloro-2-phenyl-5-pyrimidine carboxylic acid ethyl ester and 2.2 g. (0.038 mole) of allylamine in 150 ml. of ethanol was refluxed 3 hours. At this point, the solution was concentrated to 30 ml. and chilled. A yellow crystalline solid formed and was filtered off to give 4-(2-propenylamino)-2-phenyl-5-pyrimidine carboxylic acid ethyl ester--m.p. 49°-54° C. This compound was used in the next step directly without further purification.

Workup

  1. additionA mixture of 5 g
  2. concentrationAt this point, the solution was concentrated to 30 ml
  3. temperatureand chilled
  4. customA yellow crystalline solid formed
  5. filtrationwas filtered off

Sources & evidence

ORD record
ord-fb28bda985d446958b8ebe530176f883
Source dataset
uspto-grants-1981_03
Patent number
US04255568

Linked notes

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