Dichloromethane methanol → HCID 72704536, compound

HRID 1054960Notes

Reaction equation

HRID 1054960 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]([CH3:19])[N:17]=[C:16]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[N:15]=3)[N:11]=[C:4]2[N:3]=1.C(Cl)Cl.CO>[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]([CH3:19])[N:17]=[C:16]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[N:15]=3)[N:11]=[C:4]2[N:3]=1

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 131736340HCID 131736340, compound

Product 1

HCID 72704536HCID 72704536, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5,7-dimethyl-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyrimidine (65 mg, 200 μmol, Eq: 1.00) and palladium on carbon 10% (42.6 mg, 40.1 μmol, Eq: 0.2) in methanol (10.0 ml) was stirred for 14 hours at 25° C. under hydrogen atmosphere. TLC (CH2Cl2/MeOH 19:1/UV 254 nm) showed complete reaction (spot to spot). palladium was filtered off and the filtrate was evaporated and dried under high vacuum to give 5,7-Dimethyl-2-[2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-ethyl]-[1,2,4]triazolo[1,5-a]pyrimidine (34 mg, 52%) as viscous oil

Workup

  1. customreaction (spot to spot)
  2. filtrationpalladium was filtered off
  3. customthe filtrate was evaporated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-3bfaf8a2447846debbca32bdc15fe0bf
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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