8-[6-(3,6-dihydro-2H-pyran-4-yl)-2-(4-nitrophenyl)pyrimidin-4-yl]-3-oxa-8-azabicyclo[3.2.1]octane → 4-[4-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-6-(tetrahydro-2H-pyran-4-yl)pyrimidin-2-yl]aniline
Reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[N:10]=[C:9]([N:22]3[CH:27]4[CH2:28][CH2:29][CH:23]3[CH2:24][O:25][CH2:26]4)[CH:8]=2)[CH2:3][CH2:2]1>ClCCl.CC(O)C.[Pd]>[CH:23]12[N:22]([C:9]3[CH:8]=[C:7]([CH:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[N:12]=[C:11]([C:13]4[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=4)[N:10]=3)[CH:27]([CH2:28][CH2:29]1)[CH2:26][O:25][CH2:24]2Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
In a 250 mL round-bottomed flask was placed 8-(6-(3,6-dihydro-2H-pyran-4-yl)-2-(4-nitrophenyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane (74, 353 mg, 0.895 mmol) in dichloromethane (10 mL) and 2-propanol (10 mL) to give a yellow solution. Pd—C (95 mg, 0.089 mmol) was added. The reaction mixture was stirred for 72 hours under an atmosphere of hydrogen. The reaction mixture was diluted with dichloromethane, filtered through Celite™ and washed with dichloromethane. The mixture was concentrated under reduced pressure to give 324 mg of a yellow solid. HRMS: 367.2130 [M+H+. For [M+H]+ mass error=0.3 mDa or 0.7 ppm.
Workup
- customIn a 250 mL round-bottomed flask was placed
- filtrationfiltered through Celite™
- washwashed with dichloromethane
- concentrationThe mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-79bdca50411f412e9ea584aaef579a44
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835429B2
Reaction notes
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