Diisopropylethylamine → (R)-1-(5-bromo-4-methylpyrimidin-2-yl)pyrrolidin-3-ol
Reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][C@@H:4]([OH:7])[CH2:3]1.[Br:8][C:9]1[C:10]([CH3:16])=[N:11][C:12](Cl)=[N:13][CH:14]=1.CCN(C(C)C)C(C)C>CCO>[Br:8][C:9]1[C:10]([CH3:16])=[N:11][C:12]([N:2]2[CH2:6][CH2:5][C@@H:4]([OH:7])[CH2:3]2)=[N:13][CH:14]=1Participants
5
Conditions
- Temperature
- 70 °C
Procedure
In a 500 mL pear flask equipped with a magnetic stir bar were mixed (R)-pyrrolidin-3-ol hydrochloride (8.94 g, 72.3 mmol), 5-bromo-2-chloro-4-methylpyrimidine (15 g, 72.3 mmol), DIPEA (31.6 mL, 181 mmol), and EtOH (150 mL). The resulting yellow suspension was heated in a sand bath to 70° C. for 18 hours. At this time about half of the solvent was evaporated. Water (250 mL) was added to the flask while rapidly stirring the solution. An off-white precipitate formed and was filtered off, washed with water (100 mL) and dried to give the title compound (16.7 g, 89.5%).
Workup
- customIn a 500 mL pear flask equipped with a magnetic stir bar
- customAt this time about half of the solvent was evaporated
- additionWater (250 mL) was added to the flask
- customAn off-white precipitate formed
- filtrationwas filtered off
- washwashed with water (100 mL)
- customdried
Sources & evidence
- ORD record
- ord-6faf5f4fb97442599f52c3b5351843b1
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434743B2
Reaction notes
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