Acetic Acid → HCID 69961372, compound

HRID 1291311Notes

Reaction equation

HRID 1291311 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[C:7]2[C:10]([CH3:29])=[CH:11][N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:28])[C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)[C:6]=2[N:5]=[C:4]1SC)[CH3:2].C(O)(=O)C>COCCOC.C(O)C.[Ni]>[CH2:1]([N:3]1[C:8](=[O:9])[C:7]2[C:10]([CH3:29])=[CH:11][N:12]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20](=[O:28])[C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)=[CH:18][CH:19]=3)[C:6]=2[N:5]=[CH:4]1)[CH3:2]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 18919222HCID 18919222, compound

Product 1

HCID 69961372HCID 69961372, compoundYield 74.8%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
40 °C

Procedure

In a mixture of DME (50 ml) and ethanol (2 ml) was dissolved 3-ethyl-7-[4-(4-fluorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (344 mg) followed by addition of acetic acid (224 mg), and the mixture was warmed to 40° C. Then, Raney nickel was added until disappearance of the starting compound had been verified by TLC. The catalyst was then filtered off and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution in that order, and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was allowed to stand, whereupon crystals separated out. This crystal crop was harvested by filtration, rinsed with ethanol and hexane, and dried to provide the title compound (230 mg).

Workup

  1. filtrationThe catalyst was then filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customseparated out
  8. filtrationThis crystal crop was harvested by filtration
  9. washrinsed with ethanol and hexane
  10. customdried

Sources & evidence

ORD record
ord-8a2c882e02ca49bd96fd9dd682d50f00
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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