Hydrogen Bromide → 2-(2-bromopyridin-4-yl)-5-hydroxy-3-methylpyrimidin-4(3H)-one

HRID 1774435Notes

Reaction equation

C([O:8][C:9]1[C:10](=[O:23])[N:11]([CH3:22])[C:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=2)=[N:13][CH:14]=1)C1C=CC=CC=1.[BrH:24]>CC(O)=O>[Br:24][C:17]1[CH:16]=[C:15]([C:12]2[N:11]([CH3:22])[C:10](=[O:23])[C:9]([OH:8])=[CH:14][N:13]=2)[CH:20]=[CH:19][N:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-(benzyloxy)-2-(2-chloropyridin-4-yl)-3-methylpyrimidin-4(3H)-one (3.5 g, 10.7 mmol), conc. aq. HBr (10 mL), and HOAc (50 mL) was heated at 100° C. for 2 h with stirring. After cooled to rt, the solid was filtered, washed with EtOAc several times, dried to give 5 g of crude compound, which was purified by prep-HPLC to give pure 2-(2-bromopyridin-4-yl)-5-hydroxy-3-methylpyrimidin-4(3H)-one (1.9 g, 623%). 1H-NMR δ (400 MHz, d6-DMSO): 9.88 (s, 1H), 8.52 (dd, J=5.6, 0.4 Hz, 1H), 7.86 (dd, J=5.2, 0.4 Hz, 1H), 7.65 (dd, J=5.2, 1.6 Hz, 1H), 7.54 (d, J=2.0 Hz, 1H), 3.33 (s, 3H); MS (ESI) m/z. (M+H)+ 282.

Workup

temperatureAfter cooled to rt
filtrationthe solid was filtered
washwashed with EtOAc several times
customdried
customto give 5 g of crude compound, which
customwas purified by prep-HPLC

Sources & evidence

ORD record: ord-1a08eaa4302a4ddabf447654948f5aaa
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260413B2

Reaction notes

Loading…