Methyl iodide → 6-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

HRID 2096362Notes

Reaction equation

HRID 2096362 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([CH3:10])[N:7]=[C:6]([C:11]([C:13]2[CH:22]=[C:21]([CH3:23])[C:16]3[NH:17][C:18](=[O:20])[O:19][C:15]=3[CH:14]=2)=[O:12])[CH:5]=1.I[CH3:25]>CN(C=O)C>[Cl:3][C:4]1[N:9]=[C:8]([CH3:10])[N:7]=[C:6]([C:11]([C:13]2[CH:22]=[C:21]([CH3:23])[C:16]3[N:17]([CH3:25])[C:18](=[O:20])[O:19][C:15]=3[CH:14]=2)=[O:12])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 581811186-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811376-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

59 mg (1.4 mmol) sodium hydride (55%, suspension in mineral oil) were added at RT to 0.37 g (1.2 mmol) 6-(6-chloro-2-methyl-pyrimidin-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 5.0 mL. DMF. The reaction mixture was stirred for 30 min at RT. Then 0.10 ml. (1.60 mmol) iodomethane were added and the mixture was stirred for 1 h at RT. Then another 0.10 ml. (1.60 mmol) iodomethane were added and the mixture was stirred overnight at RT. The reaction mixture was diluted with ice water and the precipitate formed was suction filtered. The residue was washed with water and dried i. vac.

Workup

  1. stirringthe mixture was stirred for 1 h at RT
  2. stirringthe mixture was stirred overnight at RT
  3. customthe precipitate formed
  4. filtrationfiltered
  5. washThe residue was washed with water
  6. customdried i

Sources & evidence

ORD record
ord-861d6fbacb7f419e87ba631b1f87d77a
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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