Ammonium Chloride → 5-Methyl-2-pyrazinemethanol
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[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.ClC(OCC(C)C)=O.[BH4-].[Na+].[Cl-].[NH4+]>O1CCCC1.CO.C(N(CC)CC)C>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.ClC(OCC(C)C)=O.[BH4-].[Na+].[Cl-].[NH4+]>O1CCCC1.CO.C(N(CC)CC)C>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1
To a solution of 5-methyl-2-pyrazinecarboxylic acid (1.0 g) in tetrahydrofuran (10 mL) was added triethylamine (1.1 mL) and isobutyl chloroformate (1.0 mL), and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture was added sodium borohydride (603 mg) and methanol (5 mL) at −78° C. After stirring, to the mixture was added aqueous ammonium chloride and the mixture was extracted with ethyl acetate. The organic layer was separated and concentrated in vacuo. The resultant crude product was purified by a column chromatography on silica gel (solvent; chloroform/methanol=90:10) to give 5-methylpyrazin-2-ylmethyl alcohol (592 mg, yield: 66%).
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