1-ethyl-5-pyrrolidin-1-yl-3-trimethylsilanylethynyl-1H-[1,2,4]triazole → 1-ethyl-3-ethynyl-5-pyrrolidin-1-yl-1H-[1,2,4]triazole

HRID 1054978Notes

Reaction equation

HRID 1054978 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][Si](C)(C)C)=[N:4]1)[CH3:2]>CO.[OH-].[Na+].C(OCC)(=O)C>[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]#[CH:14])=[N:4]1)[CH3:2]

Participants

5

Reactant 1

HCID 900256441-ethyl-5-pyrrolidin-1-yl-3-trimethylsilanylethynyl-1H-[1,2,4]triazole

Product 1

HCID 900168721-ethyl-3-ethynyl-5-pyrrolidin-1-yl-1H-[1,2,4]triazoleYield 89.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-ethyl-5-(pyrrolidin-1-yl)-3-((trimethylsilyl)ethynyl)-1H-1,2,4-triazole (122 mg, 465 μmol, Eq: 1.00) in methanol (3 ml) and 1N NaOH aq. (0.1 ml) was stirred for 18 hours at 25° C. under argon atmosphere. The mixture was diluted with ethyl acetate and washed with water. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated affording 1-ethyl-3-ethynyl-5-pyrrolidin-1-yl-1H-[1,2,4]triazole (79 mg, 89.3%) as an orange oil. MS: m/z=191.2 (M+H+)

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0eb44f9ab9f349ebb90191742d90bd9e
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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