Acetic Acid → 7-[4-(4-Fluorobenzoyl)benzyl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

HRID 1291431Notes

Reaction equation

HRID 1291431 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[C:19](SC)[NH:20][C:21](=[O:22])[C:16]=4[C:15]([CH3:25])=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(O)(=O)C>COCCOC.C(OCC)(=O)C.CO.[Ni]>[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[CH:19][NH:20][C:21](=[O:22])[C:16]=4[C:15]([CH3:25])=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 176Acetic AcidHCID 1356675887-[4-(4-Fluorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 1356676097-[4-(4-Fluorobenzoyl)benzyl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-oneYield 77%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-[4-(4-Fluorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (775 mg) was dissolved in a mixture of DME (100 ml), ethyl acetate (100 ml) and methanol (80 ml). After addition of acetic acid (2.5 ml), Raney nickel was added. After confirming disapperance of the starting compound, the catalyst was filtered off. The solvent was then distilled off under reduced pressure. The residue was pulverized with ether, and the crystalline powder was collected by filtration, rinsed with ether, and dried to provide the title compound (529 mg).

Workup

  1. additionwas added
  2. filtrationthe catalyst was filtered off
  3. distillationThe solvent was then distilled off under reduced pressure
  4. filtrationthe crystalline powder was collected by filtration
  5. washrinsed with ether
  6. customdried

Sources & evidence

ORD record
ord-acc8fbc780584dc0969e924c90a7adcb
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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