Reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([N:17]2[CH:22]3[CH2:23][CH2:24][CH:18]2[CH2:19][O:20][CH2:21]3)[CH:3]=1>C(N)(C)C>[CH:22]12[N:17]([C:4]3[N:5]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=4)[N:7]=[C:2]([NH:14][CH:11]([CH3:12])[CH3:10])[CH:3]=3)[CH:18]([CH2:24][CH2:23]1)[CH2:19][O:20][CH2:21]2Participants
3
Conditions
- Temperature
- 140 °C
Procedure
In a 2-5 mL microwave vial was placed 8-(6-chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane (36, 200 mg, 0.577 mmol) in iPrNH2 (5 mL) to give a yellow suspension. The reaction was heated under microwave irradiation at 140° C. for 3×45 min. The mixture was concentrated. The residue was dissolved in dichloromethane and washed with sat NaHCO3. The organic phase was dried over MgSO4, filtered and concentrated to give the title compound (208 mg, 98%) as a yellow foam. HRMS: For [M+H]+ mass error=0.1 mDa or 0.23 ppm.
Workup
- customto give a yellow suspension
- concentrationThe mixture was concentrated
- dissolutionThe residue was dissolved in dichloromethane
- washwashed
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1bce316c12b245bfb48278a76c850844
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835429B2
Linked notes
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