C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[N:9][CH:10]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1>[S:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:8]1[N:9]=[CH:10][C:5]([CH2:3][OH:2])=[CH:6][N:7]=10.175 g of 2-thiophen-2-yl-pyrimidine-5-carboxylic acid methyl ester was dissolved in 3 mL of tetrahydrofuran. The reaction was cooled to 0° C. (ice-water bath) and then 2.39 mL of diisobutylaluminumhydride (1.0 M in tetrahydrofuran) were added dropwise. The reaction was left stirring at 0° C. for 30 minutes, then at room temperature overnight. Water was added, the mixture was extracted with ethylacetate, and the organic layer was dried with magnesium sulphate, filtered and concentrated to afford the crude (2-thiophen-2-yl-pyrimidin-5-yl)-methanol, which was used without purification for the next reactions.
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