2-(2-(1-ethyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine → 2-[2-(2-Ethyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-ethyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine

HRID 1054928Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-(2-(1-ethyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (33 mg, 97.5 μmol, Eq: 1.00) and palladium on carbon 10% (10.4 mg, 9.75 μmol, Eq: 0.1) in methanol (30 ml) was stirred for 5 hours under hydrogen atmosphere at 25° C. The catalyst was filtered off and the filtrate was evaporated affording 2-[2-(2-Ethyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-ethyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (32 mg 96.4%) as a yellow oil. MS: m/e=341.5 (M+H+)

Workup

filtrationThe catalyst was filtered off
customthe filtrate was evaporated

Sources & evidence

ORD record: ord-95a38905e5e84d0491ac99af8033bae1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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