Diisopropylethylamine → 4-Chloro-N-methyl-6-[(3R)-3-methyl-4-morpholinyl]-2-pyrimidinamine
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.CCN(C(C)C)C(C)C.[CH3:20][C@@H:21]1[CH2:26][O:25][CH2:24][CH2:23][NH:22]1>C(O)C>[Cl:8][C:6]1[CH:7]=[C:2]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][C@H:21]2[CH3:20])[N:3]=[C:4]([NH:9][CH3:10])[N:5]=1Participants
5
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 4,6-dichloro-N-methyl-2-pyrimidinamine (2 g, 11.23 mmol) in ethanol (50 mL) in a 200-mL RBF were added Hunig's base (5.89 mL, 33.7 mmol) and (3R)-3-methylmorpholine (1.546 g, 11.23 mmol). The reaction mixture was stirred at 100° C. in a sealed tube on a stirrer hotplate for 2 days. The reaction was concentrated in vacuo, and the residue was dissolved in EtOAc (200 mL) and washed with water (50 mL). The organic layer was dried over Na2SO4, filtered, then concentrated to afford the title compound (1.873 g) as a white solid. LC-MS (ES) m/z=243 [M+H]+.
Workup
- concentrationThe reaction was concentrated in vacuo
- dissolutionthe residue was dissolved in EtOAc (200 mL)
- washwashed with water (50 mL)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-79f51be833284e2fa2f112c514254ce2
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697685B2
Reaction notes
Loading…