Iodoethane → 6-(6-chloro-pyrimidine-4-carbonyl)-3-ethyl-4-methyl-3H-benzoxazol-2-one

HRID 469313

Reaction equation

HRID 469313 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.[CH2:23](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]([CH2:23][CH3:24])[C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 581812066-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811956-(6-chloro-pyrimidine-4-carbonyl)-3-ethyl-4-methyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

44 mg (1.0 mmol) sodium hydride (55%, suspension in mineral oil) were added to 0.25 g (0.86 mmol) 6-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 2.0 mL DMF and the mixture was stirred for 30 min at RT. Then 98 μL (1.2 mmol) ethyl iodide were added and the mixture was stirred for 1 h at RT. The reaction mixture was diluted with ice water and extracted with EtOAc. The organic phase was washed with water, dried on sodium sulphate, filtered and evaporated down i. vac. The residue was purified by flash chromatography. The fractions containing the product were combined and evaporated down.

Workup

  1. stirringthe mixture was stirred for 1 h at RT
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water
  4. customdried on sodium sulphate
  5. filtrationfiltered
  6. customevaporated down i
  7. customThe residue was purified by flash chromatography
  8. additionThe fractions containing the product
  9. customevaporated down

Sources & evidence

ORD record
ord-bdfc72f949b04459a75172a578251f92
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Linked notes

Loading…