4-(2-Methyl-1,3-oxazol-5-yl)aniline → 2-{6-(4-Chloro-phenyl)-2-[4-(2-methyl-oxazol-5-yl)-phenylamino]-pyrimidin-4-yl}-propan-2-ol

HRID 1855529Notes

Reaction equation

HRID 1855529 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:3]=1.[CH3:19][C:20]1[O:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)=[CH:23][N:24]=1>>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:4]2[N:3]=[C:2]([NH:31][C:28]3[CH:27]=[CH:26][C:25]([C:22]4[O:21][C:20]([CH3:19])=[N:24][CH:23]=4)=[CH:30][CH:29]=3)[N:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 15187744-(2-Methyl-1,3-oxazol-5-yl)anilineHCID 866567022-[2-Chloro-6-(4-chloro-phenyl)-pyrimidin-4-yl]-propan-2-ol

Product 1

HCID 578298042-{6-(4-Chloro-phenyl)-2-[4-(2-methyl-oxazol-5-yl)-phenylamino]-pyrimidin-4-yl}-propan-2-olYield 22.2%

Procedure

Using in analogous manner the procedure described in example 1e), 2-[2-chloro-6-(4-chloro-phenyl)-pyrimidin-4-yl]-propan-2-ol (112 mg, 0.3 mmol) was reacted with 4-(2-methyl-oxazol-5-yl)-phenylamine (61 mg, 0.3 mmol) to give the title compound as light yellow solid (28 mg, 22%). MS ISP (m/e): 421.1 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.04, 7.74, 7.63 and 7.50 (4 d, 4×2H), 7.20 (s, 1H), 7.23 (s, 1H), 7.15 (s, 1H), 4.01 (s, 1H), 2.53 (s, 3H), 1.61 (s, 6H).

Sources & evidence

ORD record
ord-3fb0814b91834b90a7730d503d9f9724
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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