METHYL 2-AMINO-6-METHOXYPYRIDINE-3-CARBOXYLATE synthesis

4synthesis methods

Product Name:METHYL 2-AMINO-6-METHOXYPYRIDINE-3-CARBOXYLATE
CAS Number:1227048-93-2
Molecular formula:C8H10N2O3
Molecular Weight:182.18

3-Pyridinecarboxylic acid, 6-methoxy-2-[[(4-methoxyphenyl)methyl]amino]-, methyl ester

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METHYL 2-AMINO-6-METHOXYPYRIDINE-3-CARBOXYLATE

1227048-93-2
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Yield:1227048-93-2 97%

Reaction Conditions:

with palladium on activated charcoal;hydrogen in ethanol at 27; for 16 h;Inert atmosphere;

Steps:

Preparation of methyl 2-amino-6-methoxynicotinate

To a stirred solution of methyl 6-methoxy-2-((4-methoxybenzyl) amino)nicotinate (16 g, 51.3 mmol) in EtOH (150 mL) at 27 °C under nitrogen atmosphere was added Pd-C(16.39 g, 15.40 mmol) portion-wise. The reaction mixture was purged with hydrogen gas and then stirred under balloon-pressure hydrogen atmosphere for 16 h. The progress of the reaction was monitored by TLC (Si02, 30% EtOAc/Pet., Rf 0.3, UV-active). Upon completion, the reaction mixture was filtered through a small pad of Celite and the filter cake was extracted with DCM (200 mL). The filtrate was concentrated under reducedpressure to obtain methyl 2-amino-6-methoxynicotinate (15 g, off-white solid). This procedure was repeated to afford a second batch of cmde product. Both batches were dissolved in EtOAc and blended. The solution was concentrated under reduced pressure to afford the combined cmde compound (32 g, 79 mmol). This material was purified by column chromatography on silica gel (Si02, 100-200 mesh) eluting with 0-30%EtOAc/Pet. The fractions containing product were collected and concentrated under reduced procedure to afford methyl 2-amino-6-methoxynicotinate (14 g, Yield: 97%, offwhite solid). ‘HNMR (400 MHz, DMSO-d6) 5 = 7.93 (d, J= 8.6 Hz, 1H), 7.28 (br s, 2H), 6.01 (d, J= 8.6 Hz, 1H), 3.82 (s, 3H), 3.76 (s, 3H). LCMS: RT = 1.89 mins, (M+H) =183.21, Purity = 99%.

References:

WO2020/95176,2020,A1 Location in patent:Page/Page column 65

38496-18-3 Synthesis

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95652-77-0 Synthesis

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