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

HRID 1054983Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-((1-ethyl-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethynyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (43 mg, 128 μmol, Eq: 1.00) and palladium on carbon 10% (13.6 mg, 12.8 μmol, Eq: 0.1) in methanol (10 ml) was stirred for 20 hours at 25° C. under hydrogen atmosphere. The catalyst was filtered off, the filtrate was evaporated affording 2-(2-(1-ethyl-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (42 mg, 96.5%) as an light yellow oil. MS: m/z=341.5 (M+H+)

Workup

filtrationThe catalyst was filtered off
customthe filtrate was evaporated

Sources & evidence

ORD record: ord-9ff37a0cbd3c45498868a71b9e14a07b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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