Hydrochloric Acid → 3-bromo-2-(hydroxymethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 405955Notes

Reaction equation

C([O:4][CH2:5][C:6]1[N:7]=[C:8]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:9]2[C:10](=[O:13])[C:11]=1[Br:12])(=O)C.Cl.O1CCOCC1.[OH-].[NH4+]>O>[Br:12][C:11]1[C:10](=[O:13])[N:9]2[C:14]([CH3:18])=[CH:15][CH:16]=[CH:17][C:8]2=[N:7][C:6]=1[CH2:5][OH:4]

Participants

Conditions

Temperature: 70 °C

Procedure

A heterogeneous mixture of (3-bromo-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)methyl acetate (4.2444 g, 13.64 mmol), concd. HCl (3.87 mL, 46.4 mmol), and 1,4-dioxane (39.0 mL) was heated with stirring at 70° C. After 3 h, the mixture was cooled to rt and the mixture was concd under reduced pressure. The residue was diluted with water (100 mL) and the pH adjusted to 10 with 28% ammonium hydroxide (10 mL). The precipitate was filtered, washed with water (200 mL), and dried under high vacuum to give 3-bromo-2-(hydroxymethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.74 (1 H, dd, J=8.8, 6.8 Hz), 7.49 (1 H, dd, J=9.0, 0.8 Hz), 7.01-7.06 (1 H, m), 5.24 (1 H, t, J=6.1 Hz), 4.52 (2 H, d, J=6.3 Hz), 2.96 (3 H, s); Mass Spectrum (ESI) m/e=268.9 [M+1 (79Br)] and 271.0 [M+1 (81Br)].

Workup

temperaturethe mixture was cooled to rt
filtrationThe precipitate was filtered
washwashed with water (200 mL)
customdried under high vacuum

Sources & evidence

ORD record: ord-698f42a250f4492b8e16b85cf9aae501
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754089B2

Reaction notes

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