Dimethylformamide → (3-bromo-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)methyl acetate

HRID 405954Notes

Reaction equation

[Br:1][C:2]1[C:7](=[O:8])[N:6]2[C:9]([CH3:13])=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH2:14]Cl.[C:16]([O-:19])(=[O:18])[CH3:17].[K+].CN(C=O)C>O>[C:16]([O:19][CH2:14][C:3]1[N:4]=[C:5]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:6]2[C:7](=[O:8])[C:2]=1[Br:1])(=[O:18])[CH3:17]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 3-bromo-2-(chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (4.5322 g, 15.76 mmol), potassium acetate (2.320 g, 23.64 mmol), and DMF (60.0 mL) was stirred at 40° C. After 3.5 h, the mixture was concd under reduced pressure. To the residue was added water (100 mL) and the resulting precipitate was collected by filtration, washed with water (100 mL), and dried to give (3-bromo-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)methyl acetate as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (1 H, dd, J=9.0, 7.0 Hz), 7.45 (1 H, dd, J=9.0, 0.8 Hz), 7.02-7.08 (1 H, m), 5.12 (2H, s), 2.95 (3 H, s), 2.14 (3 H, s); Mass Spectrum (ESI) m/e=310.9 [M+1 (79Br)] and 313.0 [M+1 (81Br)].

Workup

filtrationthe resulting precipitate was collected by filtration
washwashed with water (100 mL)
customdried

Sources & evidence

ORD record: ord-eddba022e53345db92ee8a6b7bf265a0
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754089B2

Reaction notes

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