1,2-Dimethoxyethane → HCID 54519761, compound

HRID 582006Notes

Reaction equation

HRID 582006 reaction equation
[NH2:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)[C:3]=1[C:21]#[N:22].C(COC)[O:24]C>O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Ru]>[NH2:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)[C:3]=1[C:21]([NH2:22])=[O:24]

Participants

5

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 53672099HCID 53672099, compound

Product 1

HCID 54519761HCID 54519761, compound

Reagents, catalysts & solvents 2

HCID 11981970ruthenium;triphenylphosphaneCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-amino-1-tert-butyl-4-cyano-3-(4-methoxycarbonylphenyl)pyrazole (448 mg, 1.5 mmol) and tetrakis(triphenylphosphine)ruthenium dihydride in dimethoxyethane (1 ml) and water (54 μl) was heated at 120° under a nitrogen atmosphere in a sealed tube for 18 h. The reaction was concentrated under reduced pressure and the residue subjected to column chromatography (silica 4% methanol-CH2Cl2) to give the title compound (170 mg) after recrystallisation from ethyl acetate as a colourless solid m.p. 237-239°. δH (CDCl3) 1.67 (9H, s), 4.39 (3H, s), 5.10 (2H, br s), 5.69 (2H, br s), 7.66 (2H, d, J 8.2 Hz), and 8.11 (2H, d, J 8.3 Hz).

Workup

  1. temperaturewas heated at 120° under a nitrogen atmosphere in a sealed tube for 18 h
  2. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c9d6fa57e444aafbe9f6c23ef780be8
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Reaction notes

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