2-Pyridone → 3-Bromo-1-methyl-5-(pyrimidin-4-yl)pyridin-2(1H)-one

HRID 1981506Notes

Reaction equation

[Br:1][C:2]1[C:3](=[O:14])[NH:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)[CH:7]=1.C[O-].[Na+].N1C=CC=C[C:19]1=O>CN(C)C=O.CO>[Br:1][C:2]1[C:3](=[O:14])[N:4]([CH3:19])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

20 g of 3-bromo-5-(4-pyrimidyl)-2(1H)-pyridone are suspended in 200 ml of dimethylformamide. A solution of 4.6 g of sodium methoxide in 300 ml of dry dimethylformamide and 15 ml of methanol is added to the pyridone suspension with stirring. The reaction mixture is filtered, 5.3 ml of methyl iodide are added to the filtrate and the mixture heated to 60° C. for 2 hours. After cooling to RT, the solution is concentrated in vacuo resulting in a liquid residue which crystallizes out upon addition of distilled H2O. The solid is stirred with 400 ml of distilled H2O, filtered, washed with H2O, isopropyl alcohol, and ether and dried, yielding 3-bromo-1-methyl-5-(4-pyrimidyl)-2-pyridone, M.P. 208°-210° C.

Workup

filtrationThe reaction mixture is filtered
addition5.3 ml of methyl iodide are added to the filtrate
temperatureAfter cooling to RT
concentrationthe solution is concentrated in vacuo
customresulting in a liquid residue which
customcrystallizes out upon addition of distilled H2O
stirringThe solid is stirred with 400 ml of distilled H2O
filtrationfiltered
washwashed with H2O, isopropyl alcohol, and ether
customdried

Sources & evidence

ORD record: ord-43e30e036dfb419ab4997ee52469af38
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04593028

Reaction notes

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