Sodium Methoxide → N-[2-(5-amino-1-methylpyrazol-4-yl)ethyl]formamide

To a solution of 2-(5-amino-1-methylpyrazol-4-yl)ethylamine dihydrochloride (2.98 g, 14 mmol) in methanol (50 ml) was added 28% sodium methoxide solution in methanol (5.4 ml, 28 mmol). The mixture was filtered through Celite, and the filtrate was concentrated in vacuo. A mixture of the residue and ethyl formate (80 ml) was stirred under reflux for 16 hours. To the reaction mixture was added chloroform, and the mixture was filtered through Celite. The filtrate was concentrated in vacuo to give N-[2-(5-amino-1-methylpyrazol-4-yl)ethyl]formamide (2.7 g) as a brown oil. 1H-NMR(CDCl3) δ2.57 (2H, t, J=6.9 Hz), 3.40–3.44 (2H, m), 3.67(3H, s), 5.77 (1H, br), 7.15 (1H, s), 8.16 (1H, s)

1. filtrationThe mixture was filtered through Celite
2. concentrationthe filtrate was concentrated in vacuo
3. additionA mixture of the residue and ethyl formate (80 ml)
4. temperatureunder reflux for 16 hours
5. additionTo the reaction mixture was added chloroform
6. filtrationthe mixture was filtered through Celite
7. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-f28bde5c0d784326a4183e55f98b970d

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07179801B2