Potassium Hydroxide → Methyl 2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylate

HRID 2272828Notes

Reaction equation

[NH2:1][N+:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[CH3:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:28]=1[CH:29]=O.[OH-].[K+]>O1CCOCC1.O>[CH3:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:28]=1[C:29]1[N:8]=[C:7]2[CH:6]=[CH:5][C:4]([C:9]([O:11][CH3:12])=[O:10])=[CH:3][N:2]2[N:1]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 1,6-diaminopyridin-1-ium-3-carboxylate; 2,4,6-trimethylbenzenesulfonate (6.0 g, 16.3 mmol) in 1,4-dioxane (50 mL) is added 2,6-dimethylbenzaldehyde (1.72 g, 13.00 mmol) and the reaction mixture is heated at 90° C. for 2 hours. The reaction mixture is cooled to room temperature, 1 N KOH solution (15 mL) is added, and the mixture is stirred overnight at room temperature. The reaction mixture is diluted with water (50 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts are washed with water (100 mL) and saturated brine solution (100 mL), dried over sodium sulphate, filtered, and concentrated. The crude material is purified by silica gel chromatography (combiflash) eluting with 12% EtOAc in hexanes to give the title compound as a yellow liquid (0.35 g, 16%). LCMS m/z 282 (M+H)+.

Workup

temperatureThe reaction mixture is cooled to room temperature
extractionextracted with EtOAc (2×100 mL)
washThe combined organic extracts are washed with water (100 mL) and saturated brine solution (100 mL)
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated
customThe crude material is purified by silica gel chromatography (combiflash)
washeluting with 12% EtOAc in hexanes

Sources & evidence

ORD record: ord-95fed8ce09484e7c858ef3bc0f4e2ed2
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120793B2

Reaction notes

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