Isopropanol → 6-phenyl-N4-(4-{[2-(trifluoromethyl)pyrimidin-4-yl]oxy}phenyl)pyrimidine-2,4-diamine

HRID 729986Notes

Reaction equation

HRID 729986 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1.Cl[C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:23]=[C:22]([NH2:32])[N:21]=1.C(O)(C)C.[OH-].[Na+]>O>[C:26]1([C:24]2[N:23]=[C:22]([NH2:32])[N:21]=[C:20]([NH:14][C:13]3[CH:15]=[CH:16][C:10]([O:9][C:7]4[CH:6]=[CH:5][N:4]=[C:3]([C:2]([F:1])([F:17])[F:18])[N:8]=4)=[CH:11][CH:12]=3)[CH:25]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 2408022-Amino-4-chloro-6-phenylpyrimidineHCID 288753264-((2-(Trifluoromethyl)pyrimidin-4-yl)oxy)aniline

Product 1

HCID 118450016-phenyl-N4-(4-{[2-(trifluoromethyl)pyrimidin-4-yl]oxy}phenyl)pyrimidine-2,4-diamineYield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-{[2-(trifluoromethyl)pyrimidin-4-yl]oxy}aniline (1.0 g, 3.9 mmol) and 4-chloro-6-phenylpyrimidin-2-amine (806 mg, 3.9 mmol) were suspended in water (39 mL) and isopropanol (13 mL) and the mixture was heated at 95° C. for 17 h. After cooling to rt, the mixture was neutralized with 1 N aqueous sodium hydroxide and stirred for 20 min. The precipitate were collected by filtration to afford 6-phenyl-N4-(4-{[2-(trifluoromethyl)pyrimidin-4-yl]oxy}phenyl)pyrimidine-2,4-diamine (1.2 g, 72%) as a yellow solid. 1H NMR (DMSO-d6) δ 9.35 (s, 1H), 8.85 (d, 1H), 7.85-7.91 (m, 4H), 7.42-7.47 (m, 3H), 7.30 (d, 1H), 7.18 (d, 2H), 6.48 (s, 1H), 6.38 (brs, 2H); MS ES 425 (M+H)+, calcd 425, RT=2.53 min.

Workup

  1. filtrationThe precipitate were collected by filtration

Sources & evidence

ORD record
ord-d9cba456e9be451cbe5464e4cbbd0bf2
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

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