Methyl iodide → HCID 9814006, compound

HRID 747161Notes

Reaction equation

HRID 747161 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]2[CH:14]=[CH:15][C:16](=[O:19])[NH:17][CH:18]=2)=[CH:4][N:3]=1.[CH3:20][O-].[Na+].IC>CO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]2[CH:14]=[CH:15][C:16](=[O:19])[N:17]([CH3:20])[CH:18]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 59749106HCID 59749106, compound

Product 1

HCID 9814006HCID 9814006, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-[2-amino-4-(2-furyl)-5-pyrimidinyl]-1,2-dihydro-2-pyridinone (2.2 g, 8.65 mmol) in methanol (44 ml) was added sodium methoxide (940 mg, 17.4 mmol) at room temperature under an atmosphere of nitrogen gas, followed by stirring. After 15 minutes, iodomethane (1.6 ml, 25.7 mmol) was added thereto, followed by stirring as it was for 22 hours. After concentrating the reaction mixture, water was added to the residue. Then, the precipitates were collected by filtration and washed with water, to give the crude crystals of the title compound (1.98 g). The crude crystals were suspended in ethanol, and then the precipitates were collected by filtration and washed with ethanol, to give the title compound (1.54 g, 66%) as a pale yellow solid.

Workup

  1. stirringby stirring as it
  2. waitwas for 22 hours
  3. concentrationAfter concentrating the reaction mixture, water
  4. additionwas added to the residue
  5. filtrationThen, the precipitates were collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-d4070be488314a22873d04356ae1fdc1
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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