Potassium Carbonate → HCID 50943689, compound
Reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([NH:9][C:10]3[C:15]([C:16]#[C:17][Si](C)(C)C)=[CH:14][N:13]=[C:12]([C:22]4[S:26][C:25]([C:27]([OH:30])([CH3:29])[CH3:28])=[CH:24][CH:23]=4)[N:11]=3)[NH:6][N:5]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+]>CO>[CH:1]1([C:4]2[NH:5][N:6]=[C:7]([NH:9][C:10]3[C:15]([C:16]#[CH:17])=[CH:14][N:13]=[C:12]([C:22]4[S:26][C:25]([C:27]([OH:30])([CH3:28])[CH3:29])=[CH:24][CH:23]=4)[N:11]=3)[CH:8]=2)[CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-(5-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-((trimethylsilyl)ethynyl)pyrimidin-2-yl)thiophen-2-yl)propan-2-ol (115 mg, 0.26 mmol), K2CO3 (72 mg, 0.52 mmol, 2.0 equiv.) in CH3OH (10 ml) was stirred at room temperature for 1 h. The mixture was filtered. The solid was washed with water and extracted with EtOAc. The extract was washed by brine, dried (Na2SO4), filtered and concentrated. The residue was recrystalized by ether to give compound 2-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)propan-2-ol (Compound 180) (53 mg, 55%). LC-MS (m/z)=366.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.73-0.77 (m, 2H), 0.96-1.01 (m, 2H), 1.54 (s, 6H), 1.91-1.97 (m, 1H), 4.83 (s, 1H), 5.60 (s, 1H), 6.52 (s, 1H), 7.01 (d, J=4.0 Hz, 1H), 7.69 (d, J=4.0 Hz, 1H), 8.63 (s, 1H), 8.45 (s, 1H), 8.56 (bs, 1H), 12.24 (s, 1H).