Sodium hydride → HCID 18767869, compound

HRID 480435Notes

Reaction equation

HRID 480435 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH2:11][OH:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:37])[N:22]([CH3:36])[C:23](S(C)(=O)=O)=[N:24][C:25]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:16][CH:15]=1>O1CCCC1>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:37])[N:22]([CH3:36])[C:23]([O:12][CH2:11][CH2:10][CH2:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[N:24][C:25]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31234BenzenepropanolHCID 18767977HCID 18767977, compound

Product 1

HCID 18767869HCID 18767869, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% oily suspension, 111 mg, 2.79 mmol) was added to a stirred solution of 3-phenylpropanol (387 mg, 2.85 mmol) in tetrahydrofuran (1 ml). After gas evolution ceased, 5-(4-fluorophenyl)-3-methyl-2-methylsulfonyl-6-(4-pyridyl)-4(3H)-pyrimidinone (100 mg, 0.279 mmol) was added and the mixture was heated at 60μ C. for 30 min. The reaction mixture was partitioned between dichloromethane and water. The organic solution was washed with brine, dried and evaporated. Column chromatography on silica gel (hexane-ethyl acetate=2:1) provided the title compound. MS (m/z): 416.1 (M+H)+; C25H22FN3O2 requir. 415.5.

Workup

  1. temperaturethe mixture was heated at 60μ C
  2. customThe reaction mixture was partitioned between dichloromethane and water
  3. washThe organic solution was washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-ff0d15e306e74538b07707ab6ec1ebd3
Source dataset
uspto-grants-2003_11
Patent number
US06649604B2

Reaction notes

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