Hydrogen Bromide → 2-benzyl-5-(3-fluoro-4-hydroxyphenyl)-3-methyl-3H-pyrimidin-4-one

HRID 1993343Notes

Reaction equation

Br.[CH2:2]([C:9]1[N:14]([CH3:15])[C:13](=[O:16])[C:12]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[C:19]([F:25])[CH:18]=2)=[CH:11][N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CC(O)=O>[CH2:2]([C:9]1[N:14]([CH3:15])[C:13](=[O:16])[C:12]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([F:25])[CH:18]=2)=[CH:11][N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

HBr (40%, ACS reagent grade) was added to 2-benzyl-5-(3-fluoro-4-methoxyphenyl)-3-methyl-3H-pyrimidin-4-one (Step 4, 9 g, 26 mmol) in HOAc (90 mL). The reaction was heated to 130° C. and monitored by HPLC. After 3 h, the reaction was cooled to RT and the solid was collected by filtration. The solid was washed with H2O and Et2O and dried to afford the title compound as a yellow solid. MS (ESI pos. ion) m/z: 311.1. Calc'd for C18H15FN2O2: 310.11.

Workup

temperaturethe reaction was cooled to RT
filtrationthe solid was collected by filtration
washThe solid was washed with H2O and Et2O
customdried

Sources & evidence

ORD record: ord-6a3154c5a0ad4342a3c983828a3626db
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

Loading…