6-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde synthesis

Yield:749929-24-6 80%

Reaction Conditions:

with TEMPO;[bis(acetoxy)iodo]benzene in dichloromethane at 20; for 2 h;

Steps:

A.108.2 Step 2: Preparation OF 6-METHYL L1, 2, 4]triazolo[1,5-a]pyrimidine-2-carbaldehyde

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 CH2CI2 (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/CH2CI2 to give additional amount of the aldehyde product as a while solid (12 g, 80%). 1H NMR (300 MHz, CDCI3) 6 : 2.54 (m, 3 H), 8.73 (m, 1 H), 8.85 (m, 1 H), 10.23 (m, 1 H). MS (APCI, M+H+) : 163. 1.

References:

WO2004/74270,2004,A2 Location in patent:Page 137-138