反应详情

温度

0 °C

To a 0° C. solution of 4-amino-2-phenylamino-pyrimidine-5-carbonitrile (7.00 g, 33.18 mmol) (literature prep: J Org. Chem., 1960:5711) in 170 mL of tetrahydrofuran was added 45 mL of a 1 M solution of diisobutylaluminum hydride in methylene chloride. The ice bath was removed, and an additional 40 mL of a 1 M solution of diisobutylaluminum hydride in methylene chloride was added. The reaction mixture was cooled to 0° C., and 60 mL of methanol was added dropwise. This mixture was then added to a rapidly stirring mixture of 300 mL of ethyl acetate and 250 mL of 1 N HCl. The layers were separated, and the organic layer was extracted with additional 1 N HCl. The acid layers were combined, treated with 330 mL of 1 N NaOH, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography eluting with ethyl acetate gave 4.99 g (68%) of 4-amino-2-phenylamino-pyrimidine-5-carboxaldehyde.

1. customThe ice bath was removed
2. additionan additional 40 mL of a 1 M solution of diisobutylaluminum hydride in methylene chloride was added
3. addition60 mL of methanol was added dropwise
4. additionThis mixture was then added to
5. additionmixture of 300 mL of ethyl acetate and 250 mL of 1 N HCl
6. customThe layers were separated
7. extractionthe organic layer was extracted with additional 1 N HCl
8. additiontreated with 330 mL of 1 N NaOH
9. extractionextracted with ethyl acetate
10. dry with materialThe organic layer was dried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customPurification by flash chromatography
14. washeluting with ethyl acetate