[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH2:18][C:19]#[CH:20])[C:9]1[S:10][CH:11]=[C:12]([C:14](OC)=[O:15])[N:13]=1.O>O1CCCC1>[CH3:7][N:8]([CH2:18][C:19]#[CH:20])[C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1Lithium aluminum hydride (900 mg) was added to anhydrous tetrahydrofuran (20 ml) and a solution of 2-(N-methyl-2-propynylamino)-4-methoxycarbonylthiazole (h) (5.0 g) in tetrahydrofuran (30 ml) was added dropwise thereto with stirring under ice-cooling. The mixture was refluxed for 2 hours, to which water was carefully added under ice-cooling, and evaporated to remove the tetrahydrofuran. The residue was extracted with chloroform. The extract was washed with water, dried and recrystallized from ether-hexane to give 2-(N-methyl-2-propynylamino)-4-hydroxymethylthiazole (i) (3.75 g, yield 86.5%): mp. 69°-70° C.
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