Aniline → 4-Ethylamino-2-phenylamino-pyrimidine-5-carboxylic acid ethyl ester

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:15][CH2:16][CH3:17])=[N:8][C:9](S(C)=O)=[N:10][CH:11]=1)=[O:5])[CH3:2].CCCCCC.C(OCC)(=O)C.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:15][CH2:16][CH3:17])=[N:8][C:9]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

Reactant 4

HCID 6115Aniline

HCID 8058Hexane

HCID 8857Ethyl Acetate

HCID 10634894HCID 10634894, compound

Product 1

HCID 106608644-Ethylamino-2-phenylamino-pyrimidine-5-carboxylic acid ethyl esterYield 33%

Procedure

A solution of 4-ethylamino-2-methanesulfinyl-pyrimidine-5-carboxylic acid ethyl ester (5.38 g, 20.9 mmol) in 4 mL of aniline was heated at 130° C. for 1 hour. The solution was cooled to room temperature, and 20 mL of 1:1 hexane:ethyl acetate was added. The resultant white solid was collected by filtration to give 1.96 g (33%) of the title product. The filtrate was concentrated in vacuo and purified by flash chromatography eluting with 3:1 hexane:ethyl acetate to provide an additional 257 mg (4%) of pure 4-ethylamino-2-phenylamino-pyrimidine-5-carboxylic acid ethyl ester, mp 145-147° C.