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

Participants

Reaction Steps

A mixture of (6-chloro[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol (9.86 g, 53.4 mmol), TEMPO (626 mg, 7.2 mmol), iodobenzene diacetate (18.9 g, 59 mmol) in CH2Cl2 (75 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 as a white solid (8.72 g, 90%). 1H NMR (300 MHz, CDCl3) δ: 8.93 (d, J=2.45 Hz, 1 H), 8.99 (d, J=2.64 Hz, 1 H), 10.25 (s, 1 H). MS (APCI): 183.0, 195.0 (M+H+).

Provenance & Evidence