Sodium hydride → 7-[4-(4-Chlorobenzoyl)benzyl]-1-fluoromethyl-3-methylxanthine

HRID 1291414Notes

Reaction equation

HRID 1291414 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)[C:6]=2[C:5](=[O:27])[NH:4][C:3]1=[O:28].[H-].[Na+].[F:31][CH2:32]Br>CN(C=O)C.O>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][N:7]3[C:6]4[C:5](=[O:27])[N:4]([CH2:32][F:31])[C:3](=[O:28])[N:2]([CH3:1])[C:10]=4[N:9]=[CH:8]3)=[CH:17][CH:16]=2)=[O:26])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 61108BromofluoromethaneHCID 189188013-Methyl-7-[4-(4-chlorobenzoyl)benzyl]xanthine

Product 1

HCID 189190647-[4-(4-Chlorobenzoyl)benzyl]-1-fluoromethyl-3-methylxanthineYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-7-[4-(4-chlorobenzoyl)-benzyl]xanthine (975 mg), sodium hydride (61 mg) and fluoromethyl bromide (121 mg) in DMF (10 ml) was stirred at 10° C. for 1 hour. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate =1:2) and recrystallized from ethyl acetate to provide the title compound as colorless solid (121 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate =1:2)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-195531e464604071a0ff885c35d9e304
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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