Sodium Methoxide → 1-Methyl-5-(pyrimidin-4-yl)pyridin-2(1H)-one
Reaction equation
[CH3:1][O-].[Na+].[N:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)=[N:6][CH:5]=1>CN(C=O)C.CO>[CH3:1][N:14]1[CH:15]=[C:10]([C:7]2[CH:8]=[CH:9][N:4]=[CH:5][N:6]=2)[CH:11]=[CH:12][C:13]1=[O:16]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A solution of 4.8 g of sodium methoxide in 300 ml of dry DMF and 15 ml of methanol is added to a suspension of 5-(4-pyrimidinyl)-2(1H)-pyridone (2 g) in 200 ml DMF. The reaction mixture is filtered and 5.5 ml of methyl iodide added to the filtrate. The reaction mixture is heated to 60° C. for 2 hours, cooled to RT, and the solvent evaporated in vacuo leaving a liquid residue that crystallizes upon the addition of distilled H2O. The crystalline solid is stirred with 400 ml of distilled H2O, filtered, washed with H2O, isopropyl alcohol, and ether and then air dried to yield the desired 1-methyl-5-(4-pyrimidyl)-2-pyridone, M.P. 147°-149° C.
Workup
- filtrationThe reaction mixture is filtered
- addition5.5 ml of methyl iodide added to the filtrate
- temperaturecooled to RT
- customthe solvent evaporated in vacuo
- customleaving a liquid residue
- customthat crystallizes upon the addition of distilled H2O
- filtrationfiltered
- washwashed with H2O, isopropyl alcohol, and ether
- customair dried
Sources & evidence
- ORD record
- ord-dac12006f954485fb72a957f050ed0d6
- Source dataset
- uspto-grants-1984_02
- Patent number
- US04432979
Reaction notes
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