Hydroxyamine hydrochloride → HCID 178508888, compound

Participants

Reaction Steps

To 10 mL of anhydrous methanol was added 0.33 g (14.4 mmol) of sodium metal and a solution of 0.050 g (0.72 mmol) of hydroxylamine hydrochloride in 7 mL of methanol was then added. The resulting reaction mixture was stirred for 15 minutes and 0.23 g (0.5 mmol) of methyl 5-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]thien-2-ylcarboxylate was added under nitrogen. The reaction mixture was stirred for 30 minutes, 0.011 g (0.16 mmol) of hydroxylamine hydrochloride was added, and the reaction was stirred a total of 4.5 hours, and then filtered. The filtrate was then treated with diethyl ether and the solid collected and dried in vacuo to give 0.13 g (71%) of N-{5-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]thien-2-ylcarbonyl}hydroxylamine as a tan colored solid. Rf=0.09 (10% CH3OH/CHCl3); 1H NMR (300 MHz, DMSOd6 /TFAd4) δ1.55-1.70 (m, 4H), 1.83; 1.91 (m, 1H), 2.82-2.87 (m, 4H), 3.29-3.33 (m, 1H), 6.82 (d, J=3.6 Hz, 1H), 7.43 (d, J=1.4 Hz, 1H);

Provenance & Evidence