4-(2-Dimethylaminoethyl)aniline → 2-(3-Chlorophenyl)-N-(4-(2-(dimethylamino)ethyl)phenyl)-6-ethylpyrimidin-4-amine hydrochloride

HRID 1508852Notes

Reaction equation

HRID 1508852 reaction equation
[Cl:1][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.[CH3:17][N:18]([CH3:28])[CH2:19][CH2:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>>[ClH:1].[Cl:16][C:12]1[CH:11]=[C:10]([C:4]2[N:3]=[C:2]([NH:25][C:24]3[CH:23]=[CH:22][C:21]([CH2:20][CH2:19][N:18]([CH3:17])[CH3:28])=[CH:27][CH:26]=3)[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=2)[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 149398614-(2-Dimethylaminoethyl)anilineHCID 435575804-Chloro-2-(3-chlorophenyl)-6-ethylpyrimidine

Product 1

HCID 1180373692-(3-Chlorophenyl)-N-(4-(2-(dimethylamino)ethyl)phenyl)-6-ethylpyrimidin-4-amine hydrochlorideYield 73.3%

Procedure

Following general procedure B1, 4-chloro-2-(3-chlorophenyl)-6-ethylpyrimidine (0.085 g, 0.33 mmol) was reacted with 4-(2-(dimethylamino)ethyl)aniline (0.066 g, 0.40 mmol), followed by formation of the hydrochloride salt to afford the title compound (0.101 g, 72%) as a light yellow solid. MW=417.37. 1H NMR (DMSO-d6, 500 MHz) δ 9.60 (s, 1H), 8.35-8.27 (m, 2H), 7.66 (d, J=8.5 Hz, 2H), 7.59-7.52 (m, 2H), 7.26 (d, J=8.5 Hz, 2H), 6.60 (s, 1H), 2.91-2.78 (m, 4H), 2.67 (q, J=7.5 Hz, 2H), 1.26 (t, J=7.5 Hz, 3H); APCI MS m/z 381 [M+H]+.

Sources & evidence

ORD record
ord-bfed42342d1444eba38c269caa8ba8f1
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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