3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline → (4-Benzyl-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-phenyl]-amine

HRID 1855511Notes

Reaction equation

HRID 1855511 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.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([NH2:30])[CH:21]=[CH:22][C:23]=1[C:24]1[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=1>ClCCl.C(OCC)(=O)C>[CH2:1]([C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH:30][C:20]2[CH:21]=[CH:22][C:23]([C:24]3[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=3)=[C:18]([O:17][CH3:16])[CH:19]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 584144723-methoxy-4-(1-methyl-1H-pyrazol-4-yl)anilineHCID 866336184-Benzyl-2-chloro-6-methyl-pyrimidine

Product 1

HCID 57829775(4-Benzyl-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-phenyl]-amineYield 22.2%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The title compound was prepared from 4-benzyl-2-chloro-6-methyl-pyrimidine (119 mg, 0.54 mmol) and 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-phenylamine (100 mg, 0.49 mmol) using in analogous manner the procedure described in example 206c). Column chromatography (25 g silica, dichloromethane/ethyl acetate 0-25% v/v) afforded the title compound (42 mg, 22%) as a light yellow viscous oil. MS ISP (m/e): 386.2 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.82 (s, 1H), 7.76 (m, 2H), 7.39 (d, 1H), 7.29 (m, 5H), 7.08 (s, 1H), 6.98 (dd, 1H), 6.44 (s, 1H), 3.96 (s, 2H), 3.93 (s, 3H), 3.86 (s, 3H), 2.35 (s, 3H).

Sources & evidence

ORD record
ord-50e0ca9448b84673882daed32e7ba7b2
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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