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

HRID 2096360Notes

Reaction equation

HRID 2096360 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([C:10]([C:12]2[CH:21]=[C:20]([CH3:22])[C:15]3[NH:16][C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=1.I[CH3:24]>CN(C=O)C>[Cl:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([C:10]([C:12]2[CH:21]=[C:20]([CH3:22])[C:15]3[N:16]([CH3:24])[C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 581812066-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811626-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.35 g (8.0 mmol) sodium hydride (55%, suspension in mineral oil) were added to 2.2 g (7.6 mmol) 6-(6-chloropyrimidin-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 10 mL DMF. The reaction mixture was stirred for 30 min at RT. Then 0.95 mL (15.0 mmol) iodomethane were added and the mixture was stirred for 1 h at RT. The reaction mixture was combined with ice water and the aqueous phase was extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, filtered and evaporated to dryness by rotary evaporation. The residue was triturated with diethyl ether, suction filtered and dried.

Workup

  1. stirringthe mixture was stirred for 1 h at RT
  2. extractionthe aqueous phase was extracted several times with EtOAc
  3. customThe combined organic phases were dried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness by rotary evaporation
  6. customThe residue was triturated with diethyl ether, suction
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-8132a7980736408986e5b7ec84dc3b69
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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