[CH:1]([C:3]1[N:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1)=[O:2].[BH4-].[Na+].CO.Cl>C1COCC1.[Cl-].[Na+].O>[OH:2][CH2:1][C:3]1[N:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1
To a solution of methyl 5-formylpyrazine-2-carboxylate (2.47 g) in THF (20 mL) was added sodium borohydride (170 mg) portionwise over 10 mins. After stirring for 1 h, methanol (10 mL) was added. The reaction mixture was stirred for a further 20 mins, and then HCl (1 N, aq., 20 mL) and brine (20 mL) were added. The mixture was extracted with EtOAc (3×40 mL) and the combined organic portions dried over MgSO4 and evaporated to afford the title compound (1.31 g). 1H NMR (400 MHz, CDCl3) δ ppm 4.07 (s, 3H), 4.98 (br. s., 2H), 8.80 (s, 1H), 9.27 (s, 1H)
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