Sodium Methoxide → 1-Methyl-5-(pyrimidin-4-yl)pyridin-2(1H)-one

HRID 1981509Notes

Reaction equation

HRID 1981509 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

HCID 10942334Sodium MethoxideHCID 132766775-(Pyrimidin-4-yl)pyridin-2(1H)-one

Product 1

HCID 136450941-Methyl-5-(pyrimidin-4-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

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

  1. filtrationThe reaction mixture is filtered
  2. addition5.5 ml of methyl iodide added to the filtrate
  3. temperaturecooled to RT
  4. customthe solvent evaporated in vacuo
  5. customleaving a liquid residue
  6. customthat crystallizes upon the addition of distilled H2O
  7. filtrationfiltered
  8. washwashed with H2O, isopropyl alcohol, and ether
  9. customair dried

Sources & evidence

ORD record
ord-608c70b13d1c4852bd11b915564594a9
Source dataset
uspto-grants-1986_06
Patent number
US04593028

Reaction notes

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