4-Chloro-2-(3-chlorophenyl)-6-ethylpyrimidine → Ethyl 2-(4-((2-(3-chlorophenyl)-6-ethylpyrimidin-4-yl)amino)phenyl)-3,3,3-trifluoropropanoate

HRID 1508874Notes

Reaction equation

HRID 1508874 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[N:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:30]([F:33])([F:32])[F:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=1>>[Cl:16][C:12]1[CH:11]=[C:10]([C:4]2[N:3]=[C:2]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]([C:30]([F:31])([F:32])[F:33])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=3)[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=2)[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 435575804-Chloro-2-(3-chlorophenyl)-6-ethylpyrimidineHCID 90111708Ethyl 2-(4-aminophenyl)-3,3,3-trifluoropropanoate

Product 1

HCID 90112388Ethyl 2-(4-((2-(3-chlorophenyl)-6-ethylpyrimidin-4-yl)amino)phenyl)-3,3,3-trifluoropropanoateYield 100%

Procedure

Following General Procedure A1, 4-chloro-2-(3-chlorophenyl)-6-ethylpyrimidine (0.055 g, 0.22 mmol) was reacted with ethyl 2-(4-aminophenyl)-3,3,3-trifluoropropanoate (0.080 g, 0.33 mmol) to afford the title compound (0.100 g, 100%) as an amber oil. MW=463.88. 1H NMR (CDCl3, 300 MHz) δ 8.44-8.39 (m, 1H), 8.34-8.27 (m, 1H), 7.57-7.46 (m, 4H), 7.44-7.36 (m, 2H), 6.87 (s, 1H), 6.54 (s, 1H), 4.38-4.11 (m, 3H), 2.74 (q, J=7.6 Hz, 2H), 1.40-1.21 (m, 6H); APCI MS m/z 464 [M+H]+.

Sources & evidence

ORD record
ord-c35f0f964226405381348be21cc117ab
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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