HCID 131718200, compound → HCID 131718199, compound

HRID 257257Notes

Reaction equation

HRID 257257 reaction equation
[CH:1]1([C:4]2[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[N+:31]([O-])=O)=[CH:21][CH:20]=3)=[C:7]3[N:8]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[C:11]([CH3:12])[N:6]3[N:5]=2)[CH2:3][CH2:2]1.[H][H]>[Ni].CO.C1COCC1>[CH:1]1([C:4]2[C:17]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[NH2:31])=[CH:23][CH:24]=3)=[C:7]3[N:8]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[C:11]([CH3:12])[N:6]3[N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 131718200HCID 131718200, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131718199HCID 131718199, compoundYield 168.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution/suspension of 1.59 g methyl 2-cyclopropyl-7-methyl-3-[(2'-nitrobiphen-4-yl)methyl]pyrazolo[1,5-a]pyrimidine-5-carboxylate and/0.5 g Raney Nickel in 30 mL methanol and 150 mL THF was stirred under 1 atm hydrogen for 2.5 hours. The mixture was filtered through Celite, stripped of solvent in vacuo, then was chromatographed on silica gel under medium pressure using 10% ethyl acetate in hexanes to give 2.50 g (17% yield) of the title compound as a light yellow crystalline solid. Rf 0.24 in 20% EtOAc/hexanes, visualized by UV, iodine, and ammonium molybdate/ceric sulfate stain.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customwas chromatographed on silica gel under medium pressure

Sources & evidence

ORD record
ord-be163491475c450e925224c0520f4f2e
Source dataset
uspto-grants-1993_11
Patent number
US05260285

Reaction notes

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