Cyclopropyl-{5-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine → Cyclopropyl-{5-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-ethyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine

HRID 1054970Notes

Reaction equation

HRID 1054970 reaction equation
[CH:1]1([N:4]([CH3:24])[C:5]2[N:9]=[C:8]([CH:10]=[CH:11][C:12]3[N:22]=[C:15]4[N:16]=[C:17]([CH3:21])[CH:18]=[C:19]([CH3:20])[N:14]4[N:13]=3)[N:7]([CH3:23])[N:6]=2)[CH2:3][CH2:2]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH:1]1([N:4]([C:5]2[N:9]=[C:8]([CH2:10][CH2:11][C:12]3[N:22]=[C:15]4[N:16]=[C:17]([CH3:21])[CH:18]=[C:19]([CH3:20])[N:14]4[N:13]=3)[N:7]([CH3:23])[N:6]=2)[CH3:24])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 124021668Cyclopropyl-{5-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 90017820Cyclopropyl-{5-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-ethyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amineYield 83.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 8857Ethyl AcetateSolvent

Procedure

N-cyclopropyl-5-(2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)vinyl)-N,1-dimethyl-1H-1,2,4-triazol-3-amine (10 mg, 30.8 μmol, Eq: 1.00) was stirred in Ethyl acetate (6 ml) using 5% Pd on Ba2SO4 (3 mg, 30.8 μmol, Eq: 1.00) as catalyst in a hydrogen atmosphere. The mixture was stirred at room temperature for 4 h. No reaction. Palladium on activated charcoal 10% (5 mg, 30.8 μmol, Eq: 1.00) was added an stirring was continued for 4 h. TLC showed new product but still starting material left. Palladium on activated charcoal 10% (4 mg, 30.8 μmol, Eq: 1.00) was added and stirring was continued for 4 h again. TLC showed nearly complete conversion. The crude material was applied on silica gel an purified by column chromatography using ethyl acetate/methanol (0-5% methanol) as eluent to give Cyclopropyl-{5-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-ethyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine (8.4 mg, 83.5%) as off-white semisolid.

Workup

  1. customNo reaction
  2. waitwas continued for 4 h
  3. waitleft
  4. stirringstirring
  5. waitwas continued for 4 h
  6. customan purified by column chromatography

Sources & evidence

ORD record
ord-4ef1779056804158a443355a98006177
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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