Potassium Carbonate → 6-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-5-methoxy-pyrimidin-4-ylamine

HRID 2283958Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:11]([CH3:13])[CH:12]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].Cl[C:25]1[N:30]=[CH:29][N:28]=[C:27]([NH2:31])[C:26]=1[O:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:14]3[CH2:19][CH2:18][N:17]([C:25]4[N:30]=[CH:29][N:28]=[C:27]([NH2:31])[C:26]=4[O:32][CH3:33])[CH2:16][CH2:15]3)[N:11]([CH3:13])[CH:12]=2)=[CH:4][C:3]=1[C:20]([F:21])([F:22])[F:23]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1h-imidazol-2-yl]-piperidine (40.00 mg; 0.12 mmol; 1.0 eq.), 6-chloro-5-methoxypyrimidin-4-amine (20.48 mg; 0.13 mmol; 1.05 eq.), potassium carbonate (33.78 mg; 0.24 mmol; 2.0 eq.) in DMSO (1.00 ml) in a microwave vial was heated at 150° C. for 2 h. LC-MS show ˜40% conversion and product eluted closely to the amine starting material. The reaction mixture was workup and the crude was purified by reverse phase pre-HPLC (Waters, acetonitrile/0.1% TFA in water) to yield desired product in 22% yield. LC-MS: (M+1=451, obsd.=451).

Workup

washeluted closely to the amine starting material
customthe crude was purified by reverse phase pre-HPLC (Waters, acetonitrile/0.1% TFA in water)

Sources & evidence

ORD record: ord-bbdad9acfed64556906b51da4852d509
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145392B2

Reaction notes

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