Acetic Acid → HCID 18767913, compound

HRID 398043Notes

Reaction equation

HRID 398043 reaction equation
[CH2:1](Br)[CH3:2].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12](=[O:25])[NH:13][C:14]([S:23][CH3:24])=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:7][CH:6]=1.[H-].[Na+].C(O)(=O)C>CN(C)C=O>[CH2:1]([N:13]1[C:12](=[O:25])[C:11]([C:8]2[CH:7]=[CH:6][C:5]([F:4])=[CH:10][CH:9]=2)=[C:16]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[N:15]=[C:14]1[S:23][CH3:24])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6332Ethyl Bromide2×HCID 24758Sodium hydrideHCID 135703012HCID 135703012, compound

Product 1

HCID 18767913HCID 18767913, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl bromide (600 ml, 8.03 mmol) was added to a stirred mixture of 5-(4-fluorophenyl)-2-methylthio-6-(4-pyridyl)-4(3H)-pyrimidinone (1.8 g, 5.97 mmol) and sodium hydride (60% oily suspension, 320 mg, 8 mmol) in N,N-dimethylformamide (60 ml) at room temperature. More ethyl bromide (2×600 ml, 2×8.03 mmol) was added after 2 and 3.5 h. After 8 h, the reaction mixture was neutralized with acetic acid and evaporated. The remainder was taken up in dichloromethane, the organic solution was washed with water, dried and evaporated. Flash chromatography on a column of silica gel (hexane-acetone=3:1, 2:1). provided in the second main fraction the title compound as a solid.

Workup

  1. customevaporated
  2. washthe organic solution was washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-6188a75c31e0449697f5643c3d5df3cc
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

Loading…