反应详情

6-[2-(3-Chloro-4-isopropoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione (0.3 g, 0.79 mmol) and 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde (0.17 g, 0.95 mmol, described in Step 3 of example B(75)) were dissolved in 3:1 MeOH/CH2Cl2 (4 mL). To this suspension, Me2NH.BH3 (0.07 g, 1.19 mmol) was added as a solid from top. After stirring 1 h at room temperature, the reaction mixture became clear and it was stirred for an additional 5 hours. After this time, 1 M HCl (1 mL) was added and the reaction stirred for 30 minutes at room temperature, the solvent was the evaporated to half the volumen and extracted 3 times with 10% MeOH/CH2Cl2 (10 mL). The organic phase was dried over MgSO4 and evaporated. The residue purified by flash column chromatography (80% EtOAc in hexanes) to eliminate unreacted pyrone and reduced 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde, then 3% MeOH/CH2Cl2 to give the product (0.1 g, 24%) as a white solid.

1. additionBH3 (0.07 g, 1.19 mmol) was added as a solid from top
2. stirringit was stirred for an additional 5 hours
3. stirringthe reaction stirred for 30 minutes at room temperature
4. customevaporated to half the volumen
5. extractionextracted 3 times with 10% MeOH/CH2Cl2 (10 mL)
6. dry with materialThe organic phase was dried over MgSO4
7. customevaporated
8. customThe residue purified by flash column chromatography (80% EtOAc in hexanes)