2-(2-(3-(azetidin-1-yl)-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine → 2-[2-(5-azetidin-1-yl-2-methyl-2H-[1,2,4]triazol-3-yl)-ethyl]-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1054956Notes

Reaction equation

HRID 1054956 reaction equation
[N:1]1([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)[CH2:4][CH2:3][CH2:2]1>[Pd].CO>[N:1]1([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)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 1235115082-(2-(3-(azetidin-1-yl)-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 727045342-[2-(5-azetidin-1-yl-2-methyl-2H-[1,2,4]triazol-3-yl)-ethyl]-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidineYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-(2-(3-(azetidin-1-yl)-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine (15 mg, 48.3 μmol, Eq: 1.00) and palladium on carbon 10% (5.14 mg, 4.83 μmol, Eq: 0.1) in methanol (15 ml) was stirred for 6 hours at 25° C. under hydrogen atmosphere. The catalyst was filtered off, evaporation of the solvent afforded 2-[2-(5-azetidin-1-yl-2-methyl-2H-[1,2,4]triazol-3-yl)-ethyl]-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine (14.3 mg/94.7%) as a light yellow solid. MS: m/z=313.4 (M+H+).

Workup

  1. filtrationThe catalyst was filtered off
  2. customevaporation of the solvent

Sources & evidence

ORD record
ord-e3e1d5e9a8b94daaa8218e837c796c20
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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