Potassium Carbonate → tert-Butyl 4-(4-((4-ethynyl-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate
Reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]([F:45])([F:44])[C:9]1[C:10]([C:35]#[C:36][Si](CC)(CC)CC)=[N:11][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[N:13][CH:14]=1>CO.O>[C:35]([C:10]1[C:9]([C:8]([F:44])([F:7])[F:45])=[CH:14][N:13]=[C:12]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[N:11]=1)#[CH:36]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of K2CO3 (1.72 g, 12.4 mmol) and tert-butyl 4-(4-((5-(trifluoromethyl)-4-((triethylsilyl)ethynyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate A50 (4.64 g, 8.28 mmol) in MeOH (250 mL) was stirred for 15 minutes at room temperature. The mixture was diluted with water (250 mL) and extracted with DCM (3×250 mL). The organics were combined and adsorbed onto silica gel. Purification by silica gel column chromatography (Biotage Isolera, 0-100% EtOAc in petroleum benzine 40-60° C.) gave the title compound A51 as a yellow solid (2.196 g, 59%). LCMS-A: rt 6.615 min; m/z 445 [M−H]−.
Workup
- extractionextracted with DCM (3×250 mL)
- customPurification by silica gel column chromatography (Biotage Isolera, 0-100% EtOAc in petroleum benzine 40-60° C.)
Sources & evidence
- ORD record
- ord-24e53ebc769442649b6cfe72a115f8df
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238644B2
Reaction notes
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