Sodium hydride → HCID 18767869, compound

HRID 2229778Notes

Reaction equation

HRID 2229778 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

Conditions

Temperature
60 °C

Procedure

Sodium hydride (60% oily suspension, 111 mg, 2.79 mmol) was added to a stirred solution of 3-phenylpropanol (387mg, 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 60° 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. customThe reaction mixture was partitioned between dichloromethane and water
  2. washThe organic solution was washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-5b574414160b4540bd79e09219c8179b
Source dataset
uspto-grants-2002_07
Patent number
US06420385B1

Reaction notes

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