(S)-N4-(1-(5-Fluoropyridin-2-yl)ethyl)-N2-(2-methoxypyridin-3-yl)pyrimidine-2,4-diamine → (S)-3-(4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidin-2-ylamino)pyridin-2(1H)-one
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[C:19]([O:24]C)=[N:20][CH:21]=[CH:22][CH:23]=3)[N:12]=2)[CH3:9])=[N:6][CH:7]=1>Br.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[C:19](=[O:24])[NH:20][CH:21]=[CH:22][CH:23]=3)[N:12]=2)[CH3:9])=[N:6][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A suspension of (S)—N4-(1-(5-fluoropyridin-2-yl)ethyl)-N2-(2-methoxypyridin-3-yl) pyrimidine-2,4-diamine (Preparation 1 b, 11 mg, 0.03 mmol) in 48% aqueous hydrogen bromide solution (2 mL) was stirred and heated to 100° C. for 5 hours. After cooling to ambient temperature, the reaction mixture was diluted with water and extracted with dichloromethane. The pH of the aqueous phase was then adjusted to ca. 8 with 2M aqueous sodium hydroxide solution and extracted (×3) with dichloromethane. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered and the solvent evaporated under reduced pressure to yield the title compound (4 mg, 38%) as a solid.
Workup
- temperatureAfter cooling to ambient temperature
- extractionextracted with dichloromethane
- extractionextracted (×3) with dichloromethane
- washThe combined organic extracts were washed with water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-2feaf2457b1f4926a4cca6c3fd3bfcd4
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034311B2
Reaction notes
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