Sodium borohydride → HCID 90931501, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:35])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:20]4[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]4)[N:18]=[CH:19][C:14]3=[C:13]([N:27]3[CH2:33][CH:32]4[O:34][CH:29]([CH2:30][CH2:31]4)[CH2:28]3)[N:12]=2)=[CH:7][CH:6]=1.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:35])[NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:20]4[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]4)[N:18]=[CH:19][C:14]3=[C:13]([N:27]3[CH2:33][CH:32]4[O:34][CH:29]([CH2:30][CH2:31]4)[CH2:28]3)[N:12]=2)=[CH:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl{4-[4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1-(4-oxocyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate (63 mg) (0.13 mmol) in THF (2.0 mL) was added an excess of sodium borohydride. The mixture was stirred for 1 hr. at 50 C. The reaction was then cooled and quenched with water and extracted three times with EtOAc. Organics were dried (MgSO4) and concentrated in vacuo. The resulting oil was triturated with diethyl ether to give a white solid. The solid was filtered and washed the diethyl ether to give (44 mg) MS m/z=479.2 (M+H).