Sodium Bicarbonate → Methyl 4-amino-6-(1-hydroxyethyl)-3-methoxypicolinate

Participants

Reaction Steps

To a 0° C. solution of methyl 6-acetyl-4-amino-3-methoxypicolinate (0.75 g, 3.35 mmol) in MeOH (11.15 ml) was added sodium borohydride (0.127 g, 3.35 mmol) by portion. The reaction mixture was stirred at room temperature (TLC monitoring). After 2 h, the reaction mixture was poured into saturated NaHCO3 and extracted with EtOAc (2×) and CH2Cl2 (1×). The combined organic layers were dried over MgSO4, filtered, concentrated and dried in vacuo to afford methyl 4-amino-6-(1-hydroxyethyl)-3-methoxypicolinate (0.548 g, 2.422 mmol, 72.4% yield) as a brown oil, which was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) δ 6.72 (s, 1H), 4.76 (q, J=6.4 Hz, 1H), 4.52 (s, 2H), 3.96 (s, 3H), 3.94 (s, 1H), 3.86 (s, 3H), 1.45 (d, J=6.5 Hz, 3H).

Provenance & Evidence