3-Methyl-4-pyridinamine → 2-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methylpyridin-4-yl)amide

A solution of 4-amino-3-methylpyridine (0.11 g) in dry N,N-dimethylformamide (20 ml) was stirred at 0° C. under an atmosphere of dry nitrogen. Sodium bis(trimethylsilyl)amide (1.0M solution in tetrahydrofuran, 1.0 ml) was added and stirring continued at 0° C. for 10 minutes. 2-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.20 g) was added and stirring continued at room temperature for 90 minutes. The solvent was then removed in vacuo, the residue taken up in water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water (100 ml), then brine (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with ethyl acetate gave the title compound (0.15 g) as a white solid.

1. stirringstirring
2. waitcontinued at room temperature for 90 minutes
3. customThe solvent was then removed in vacuo
4. extractionextracted with ethyl acetate (3×100 ml)
5. washThe combined organic extracts were washed with water (100 ml)
6. dry with materialbrine (50 ml), dried over magnesium sulfate
7. filtrationfiltered
8. customthe solvent removed in vacuo
9. customPurification by column chromatography on silica eluting with ethyl acetate

ORD record

ord-bceb532c9c9a447abcb1f89167b54ca4

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06169090A