Water → 5-Bromo-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-4-ylamine

HRID 2283950Notes

Reaction equation

HRID 2283950 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[N:20]([CH3:22])[CH:21]=2)=[CH:13][C:12]=1[C:29]([F:32])([F:31])[F:30].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1[N:26]1[CH2:27][CH2:28][CH:23]([C:19]2[N:20]([CH3:22])[CH:21]=[C:17]([C:14]3[CH:15]=[CH:16][C:11]([F:10])=[C:12]([C:29]([F:32])([F:30])[F:31])[CH:13]=3)[N:18]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 866320214-(4-(4-Fluoro-3-(trifluoromethyl)phenyl)-1-methyl-1H-imidazol-2-yl)piperidine

Product 1

HCID 894425615-Bromo-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-4-ylamineYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-6-chloropyrimidin-4-amine (357.2 mg; 1.71 mmol; 1.02 eq.), 4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1h-imidazol-2-yl]-piperidine (550.00 mg; 1.68 mmol; 1.0 eq.), potassium carbonate (464.4 mg; 3.36 mmol; 2.0 eq.) in DMSO (6.0 ml) was stirred at 60° C. overnight. The reaction mixture was poured into water. The precipitate was filtered, washed with water and dried under vacuum to afford the title compound in 86% yield. LC-MS: (M+1=499, obsd.=499).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-2cd4a6c6c7234c2faff684fa1670ead9
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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