[CH:1]([C:3]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=1)=O.[CH3:12][NH:13][CH3:14].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:12][N:13]([CH2:1][C:3]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=1)[CH3:14]
To a solution of 6-formyl-2-pyridinecarboxylic acid (available from Chemstep Product List, 250 mg, 1.65 mmol) in dichloromethane (4.6 ml) was added dimethylamine (2M solution in THF, 2.17 ml, 4.34 mmol) and acetic acid (0.083 ml). The mixture was stirred at room temperature for 15 mins when sodium triacetoxyborohydride (459 mg, 2.17 mmol) was added and the mixture stirred overnight. The reaction mixture was quenched by the addition of a few drops of methanol. The mixture was loaded onto an aminopropyl-SPE cartridge (5 g) pre-eluted with dichloromethane, which was eluted with dichloromethane followed by methanol. Fractions containing product were combined and dried under vacuum. The crude product was taken up in sodium hydroxide solution (2M, 25 ml) and washed with dichloromethane (2×25 ml). The aqueous layer was acidified to pH7 using hydrochloric acid (5M) and concentrated under vacuum to approximately 25 ml. The solution was loaded onto an Oasis cartridge (6 g), which had been pre-eluted with methanol (1 volume) followed by water (1 volume). The cartridge was eluted with water (1 volume) followed by methanol. Fractions containing product were combined and dried to give the title compound (85 mg).
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