methyl 2-(6-aminopyridin-3-yl)acetate synthesis
- Product Name:methyl 2-(6-aminopyridin-3-yl)acetate
- CAS Number:174891-02-2
- Molecular formula:C8H10N2O2
- Molecular Weight:166.18
Yield:174891-02-2 18%
Reaction Conditions:
Stage #1: methanol;2-(6-aminopyridin-3-yl)acetic acid hydrochloridewith sulfuric acid in water;Reflux;
Stage #2: with sodium hydrogencarbonate in water; pH=8.0;
Steps:
To a solution of intermediate (l-30e) (11.0 g, 72.36 mmol) in dry methanol (80 mL) was added cone. H2SO4 (1.6 mL) and heated to reflux overnight. LC-MS indicated the reaction was complete. The reaction mixture was basified to pH 8.0 with sat. aq. sodium bicarbonate and extracted with ethyl acetate (30 ml_ x 3). The combined organic layer was dried and concentrated in vacuo to give a crude product, which was purified by prep. HPLC to afford (1-3Of) (2.2 g, yield: 18%) as a white solid; 1H NMR (400 MHz, CD3OD): δ 7.78-7.82 (1 H), 7.40-7.50 (1 H), 6.59-6.62 (1 H), 3.69-3.78 (3 H), 3.50-3.60 (2 H); m/z 167.3 (M+H)+.
References:
WO2010/29461,2010,A1 Location in patent:Page/Page column 70-71
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