1-Methyl-1H-1,2,3-triazole → HCID 114685151, compound

HRID 1478480Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[N:3]1.C([Li])CCC.[CH3:12][N:13]1[C:17]([CH:18]=[O:19])=[CH:16][N:15]=[CH:14]1>C1COCC1>[CH3:1][N:2]1[C:6]([CH:18]([C:17]2[N:13]([CH3:12])[CH:14]=[N:15][CH:16]=2)[OH:19])=[CH:5][N:4]=[N:3]1

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of 1-methyl-1H-1,2,3-triazole (1.47 g, 17.7 mmol, PCT Int. Appl. 2008098104) in 20 mL THF was cooled to −40° C. in a dry-ice/acetonitrile bath. n-Butyllithium (1.6 M in hexane, 10.2 mL, 16.3 mmol) was added dropwise via syringe and the mixture was stirred at −40° C. for 30 minutes. A solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.50 g, 13.6 mmol) in 10 mL THF was then added and the mixture was stirred for 5 minutes, then was transferred to an ice/water bath. After 1 hour, the mixture was quenched by addition of saturated aqueous NH4Cl, diluted with water, and extracted twice with EtOAc. The aqueous phase, which contained the title compound, was then concentrated. The residue was purified by flash column chromatography (silica gel, gradient 3-10% MeOH-DCM) to afford the title compound as a light yellow foam.

Workup

stirringthe mixture was stirred for 5 minutes
customwas transferred to an ice/water bath
waitAfter 1 hour
customthe mixture was quenched by addition of saturated aqueous NH4Cl
additiondiluted with water
extractionextracted twice with EtOAc
concentrationwas then concentrated
customThe residue was purified by flash column chromatography (silica gel, gradient 3-10% MeOH-DCM)

Sources & evidence

ORD record: ord-32a21fb903bd442f9b31a12d4c5a56c0
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403816B2

Reaction notes

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