Triethylamine → (3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-pyrimidin-2-yl)-amine

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.Cl[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[NH2:19])[O:14][CH3:15].C(N(CC)CC)C.C(Cl)(Cl)[Cl:28].CCCCCC>>[Cl:28][C:12]1[CH:11]=[C:18]([NH:19][C:2]2[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=2)[CH:17]=[CH:16][C:13]=1[O:14][CH3:15]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 773782,4,6-Trichloropyrimidine

HCID 4074322-Chloro-4-methoxyaniline

HCID 21585165Chloroform hexane

Product 1

HCID 58626087(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-pyrimidin-2-yl)-amineYield 22%

Procedure

To a solution of 2,4,6-trichloro-pyrimidine (0.29 g, 1.58 mmol) in 1:1 chloroform-hexane (10 mL) was added 3-chloro-p-anisidine (0.5 g, 3.1 mmol) at 25° C. with stirring. To this was added triethylamine (0.22 mL, 1.59 mmol) at 25° C. and the mixture was heated and refluxed for 7 hours under nitrogen atmosphere. The mixture was then concentrated under vacuum, diluted with cold water (30 mL) and extracted with ethyl acetate (2×60 mL). The organic layers were collected, combined, washed with brine (30 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum. The crude product thus obtained was purified by column chromatography using ethyl acetate-petroleum ether to afford the desired compound. Yield: 22%.