4-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenylamine → (4-Benzyl-6-methyl-pyrimidin-2-yl)-[4-(2,4-dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-amine

HRID 1855508Notes

Reaction equation

HRID 1855508 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][C:17]1[S:18][C:19]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][C:24]=2[O:30][CH3:31])=[C:20]([CH3:22])[N:21]=1>ClCCl.C(OCC)(=O)C>[CH2:1]([C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH:29][C:26]2[CH:27]=[CH:28][C:23]([C:19]3[S:18][C:17]([CH3:16])=[N:21][C:20]=3[CH3:22])=[C:24]([O:30][CH3:31])[CH:25]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 670962794-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenylamineHCID 866336184-Benzyl-2-chloro-6-methyl-pyrimidine

Product 1

HCID 57829792(4-Benzyl-6-methyl-pyrimidin-2-yl)-[4-(2,4-dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-amineYield 94.6%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The title compound was prepared from 4-benzyl-2-chloro-6-methyl-pyrimidine (130 mg, 0.59 mmol) and 4-(2,4-dimethyl-thiazol-5-yl)-3-methoxy-phenylamine (139 mg, 0.49 mmol) using in analogous manner the procedure described in example 206c). Column chromatography (20 g silica, dichloromethane/ethyl acetate 1/1 v/v) afforded the title compound (193 mg, 78%) as a light yellow waxy solid. MS ISP (m/e): 417.2 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.78 (d, 1H), 7.29 (m, 5H), 7.17 (d, 1H), 7.14 (s, 1H), 6.99 (dd, 1H), 6.48 (s, 1H), 3.97 (s, 2H), 3.78 (s, 3H), 2.67 (s, 3H), 2.37 (s, 3H), 2.32 (s, 3H).

Sources & evidence

ORD record
ord-97635bec5228498c90c1b2ca3414278f
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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