3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)aniline → (4-Benzyl-6-methyl-pyrimidin-2-yl)-[3-fluoro-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 1855472Notes

Reaction equation

HRID 1855472 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10](Cl)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19]([NH2:29])[CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1>ClCCl>[CH2:1]([C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH:29][C:19]2[CH:20]=[CH:21][C:22]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[C:17]([F:16])[CH:18]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 218766383-Fluoro-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 866336184-Benzyl-2-chloro-6-methyl-pyrimidine

Product 1

HCID 57829769(4-Benzyl-6-methyl-pyrimidin-2-yl)-[3-fluoro-4-(4-methyl-imidazol-1-yl)-phenyl]-amineYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 4-benzyl-2-chloro-6-methyl-pyrimidine (100 mg, 0.46 mmol) and 3-fluoro-4-(4-methyl-imidazol-1-yl)-phenylamine (88 mg, 0.57 mmol) using in analogous manner the procedure described in example 43b). Column chromatography (15 g silica, dichloromethane+3.7% methanol v/v) afforded the title compound (148 mg, 86%) as a white solid. MS ISP (m/e): 374.4 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.98 (dd, 1H), 7.65 (s, 1H), 7.26 (m, 8H), 6.92 (s, 1H), 6.53 (s, 1H), 3.98 (s, 2H), 2.38 8s, 3H), 2.31 (s, 3H). Mp 155-158° C.

Sources & evidence

ORD record
ord-55eb6b21a08242c1a0678fdf6b34a7b9
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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