Chloride → 8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[-1,5-a]pyrimidine-2-carbaldehyde

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Reaction Conditions

Reaction Steps

To a round bottomed flask was loaded 0.17 ml of DMSO and 1 ml dichloromethane. The mixture was cooled to −50˜−60° C. Then a mixture of 0.1 ml oxallyl chloride and 2 ml dichloromethane was injected in into the flask all at once. The mixture was stirred at the same temperature for another 5 minutes. Then 0.174 grams of (8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-methanol in 2 ml dichloromethane was added within 2 minutes. The mixture was stirred at −50˜−60° C. for fifteen minutes and 0.7 ml triethylamine was next added. After another five minutes the reaction media was warmed up to 23° C. and a mixture of 20 ml water and 200 ml dichloromethane was added. The organic layer was dried over magnesium sulfate. Filter off the drying agent and concentrate the filtrate yielded 0.153 grams of product (89%). MS: 203.1 (M+H). H-NMR (CDCl3): δ 10.24 (s, 1H), 3.49 (m, 2H), 3.15 (m, 2H), 2.67 (s, 3H, CH3), 2.44 (m, 2H, CH2).

Provenance & Evidence