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

HRID 469345Notes

Reaction equation

HRID 469345 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-pyrimidine-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-dc352da25d2f4e6a9b5dcd7b6d5d03d8
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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