N-methoxy-N-methyloxane-4-carboxamide → HCID 86640819, compound

Participants

Reaction Conditions

Reaction Steps

(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)(tetrahydro-2H-pyran-4-yl)methanone. 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (11.07 g, 52.0 mmol) was suspended in anhydrous tetrahydrofuran (200 mL) and cooled to −78° C. n-Butyllithium (71.4 mL, 114 mmol) was added over 30 min and the solution was allowed to stir for 2 h (brown suspension) at −78° C. N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide (9 g, 52.0 mmol) dissolved in tetrahydrofuran (50 mL, dried over molecular sieves) was added dropwise via syringe. The reaction was stirred for 1 h at −78° C. and allowed slowly warm to room temperature for 3 h (reaction became clear solution as it warmed up to room temperature.). LCMS analysis showed the desired product. The reaction was quenched with saturated sodium bicarbonate solution. The layers were separated and the aqueous was extracted with ethyl acetate (2×200 mL). The organics were dried with sodium sulfate, and the volatiles removed in vacuo. The crude was purified by crystallization from ethyl acetate to give (2-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)(tetrahydro-2H-pyran-4-yl)methanone (8.4 g, 34.1 mmol, 65.6% yield) as a yellow solid. MS (ESI) m/z 247.0 [M+1]+.

Provenance & Evidence