Methyl 4-aminopyridine-3-carboxylate

Off-white solid

[4-TERT-BUTOXYCARBONYLAMINO-NICOTINIC] acid methyl ester (9.08 g, 36.0 [MMOL)] was dissolved in 50/50 TFA/DCM (100 mL) solution and stirred for 2 hours at room temperature. Concentration of the mixture under reduced pressure was followed by [RE-DISSOLUTION] in DCM (100 mL), washing with saturated sodium bicarbonate, drying over sodium sulfate, and concentration under reduced pressure. The corresponding de- protected product of Formula 505, 4-amino-nicotinic acid methyl ester (5.43 g, 99.1percent) was obtained was obtained in sufficient purity to be carried forward for use in the next step. MS [(CI)] M/E: 153.1.Methyl4- (Boc-amino) pyridine-3-carboxylate (2.38 g, 9.4 mmol) was dissolved in TFA (20 mL) and the solution was allowed to stir for 45 min. The solvent was removed in vacuo and the residue was partitioned between 25percent isopropanol in chloroform and satd aq sodium bicarbonate. The layers were separated and the aqueous phase was extracted again with 25percent isopropanol in chloroform. The combined organic extracts were dried(MgSO4), filtered and concentrated in vacuo to give a solid which was washed with diisopropyl ether and dried in vacuo to give the title compound (1. 327 g, 92percent) as an off-white solid. 1NMR' IS-MS, m/e 153.1 (mol) Analysis for C7H8N2 2 : Calcd : C, 55.26 ; H, 5.30 ; N, 18.41 ; Found: C, 55.31 ; H, 5.36 ; N, 18. 42.In a CEM microwave vial, 3-methyl-5-nitro-pyrimidin-4-one (300 mg, 1.94 mmol), methylacetoacetate (2.7 g, 23.27 mmol), ammonium acetate (1.79 g, 23.22 mmol) and MeOH (8.0mL) were added and irradiated at 80 °C for 2 h (TLC indicated complete consumption ofstarting material). The reaction mixture was concentrated under reduced pressure to give thecrude product which was purified by column chromatography (100-200 silica gel, 40 g, 5-10percent MeOH-DCM) to afford methyl 4-aminopyridine-3-carboxylate; this reaction mixturewas carried out in 6 batches (300 mg each), the crude material after work-up was combinedand purified to afford methyl 4-aminopyridine-3-carboxylate (900 mg, 51percent) as a yellowsolid.LCMS (ESI+): m/z: 153.43 [M+Ht.Step a): Methyl 4-aminopyridine-3-carboxylate To a solution of 4-aminopyridine-3-carboxylic acid (17 g, 0.123 mol) in MeOH (300 mL) was added H

Molecular Weight:152.15
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:152.058577502
Monoisotopic Mass:152.058577502
Topological Polar Surface Area:65.2
Heavy Atom Count:11
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes