5,7-dimethyl-2-(2-(3-(pyrrolidin-1-yl)-1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyrimidine → 5,7-dimethyl-2-{2-[5-pyrrolidin-1-yl-2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-ethyl}-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1054958Notes

Reaction equation

HRID 1054958 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([CH:12]=[CH:13][C:14]3[N:18]([CH2:19][C:20]([F:23])([F:22])[F:21])[N:17]=[C:16]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)[N:15]=3)[N:11]=[C:4]2[N:3]=1>[Pd].CO>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([CH2:12][CH2:13][C:14]3[N:18]([CH2:19][C:20]([F:23])([F:21])[F:22])[N:17]=[C:16]([N:24]4[CH2:25][CH2:26][CH2:27][CH2:28]4)[N:15]=3)[N:11]=[C:4]2[N:3]=1

Participants

4

Reactant 1

HCID 1236049185,7-dimethyl-2-(2-(3-(pyrrolidin-1-yl)-1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 727045355,7-dimethyl-2-{2-[5-pyrrolidin-1-yl-2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-ethyl}-[1,2,4]triazolo[1,5-a]pyrimidineYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5,7-dimethyl-2-(2-(3-(pyrrolidin-1-yl)-1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyrimidine (19 mg, 48.4 μmol, Eq: 1.00) and palladium on carbon 10% (5.15 mg, 4.84 μmol, Eq: 0.1) in methanol (15 ml) was stirred for 6 hours at 25° C. under hydrogen atmosphere. Evaporation of the solvent afforded 5,7-dimethyl-2-{2-[5-pyrrolidin-1-yl-2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-ethyl}-[1,2,4]triazolo[1,5-a]pyrimidine (19 mg/99.5%) as a white solid. MS: m/z=395.5 (M+H+), mp: 180.2° C.

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b58c2c1e32704d9e8e501d55339f6c8c
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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