Hydrogen Bromide → N-(5-(Bromomethyl)-4-(4-fluorophenyl)-6-(1-methylethyl)-2-pyrimidinyl)-N-methylmethanesulfonamide

HRID 445926Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14]O)=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[C:10]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[N:9]=2)=[CH:4][CH:3]=1.[BrH:25]>C(OCC)(=O)C.CCCCCC>[Br:25][CH2:14][C:13]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][C:10]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[N:11][C:12]=1[CH:16]([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

N-[4-(4-fluorophenyl)-5-hydroxymethyl-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (50.0 g) and 48% hydrogen bromide (130.0 mL) were added to a reactor. The reaction mixture was stirred at 80° C. for 15 hours. The reaction was monitored with thin layer chromatography (ethyl acetate/n-hexane=1:2). The reaction mixture was cooled to 20˜25° C., stirred for over 1 hour, and then filtered under reduced pressure. The resulting white solid was washed with water (500.0 mL) and then dried under reduced pressure to obtain N-[5-bromomethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide as a white solid (55.3 g, yield 94%).

Workup

temperatureThe reaction mixture was cooled to 20˜25° C.
stirringstirred for over 1 hour
filtrationfiltered under reduced pressure
washThe resulting white solid was washed with water (500.0 mL)
customdried under reduced pressure

Sources & evidence

ORD record: ord-9d031f87053e4d90bc1547dd4b2400df
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476432B2

Reaction notes

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