tert-Butyl methyl ether → 6-Methyl-[1,2,4]triazolo[1,5-A]pyrimidine-2-carbaldehyde

Participants

Reaction Steps

A mixture of (6-methyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol (15.7 g, 95.6 mmol), TEMPO (1.12 mg, 7.2 mmol), iodobenzene diacetate (33.9 g, 105.2 mmol) in CH2Cl2 (100 mL) was stirred at room temperature for 2 hours. Once the reaction was deemed complete, methyl-tert-butyl ether (50 mL) was added slowly to precipitate the product. The concentrated mother liquor was introduced into a silica gel column and eluted with 2% MeOH/CH2Cl2 to give additional amount of the aldehyde product as a while solid (12 g, 80%). 1H NMR (300 MHz, CDCl3) δ: 2.54 (m, 3H), 8.73 (m, 1H), 8.85 (m, 1H), 10.23 (m, 1H). MS (APCI, M+H+): 163.1.

Provenance & Evidence