反应详情

1,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-5-carboxylic acid made by the method of Example 8a) (3.316 g), triethylamine (1.38 ml) and diphenylphosphoryl azide (2.26 ml) were heated at 90° C. under an atmosphere of nitrogen in tert-butanol for 18 hrs. The reaction was concentrated in vacuo and the residue redissolved in dichloromethane (50 ml) and trifluoroacetic acid (30 ml). The mixture was allowed to stir for 36 hrs before being concentrated in vacuo, and residual acid was removed by azeotroping with toluene. The residue was partitioned between half saturated sodium hydrogen carbonate and dichloromethane. The organics were collected, dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by chromatography, eluting with 2:1 isohexane:diethyl ether to yield a highly crystalline solid which was recystallised from dichloromethane/isohexane to yield the subtitle compound (1.553 g).

1. concentrationThe reaction was concentrated in vacuo
2. dissolutionthe residue redissolved in dichloromethane (50 ml)
3. concentrationbefore being concentrated in vacuo, and residual acid
4. customwas removed
5. customby azeotroping with toluene
6. customThe residue was partitioned between half saturated sodium hydrogen carbonate and dichloromethane
7. customThe organics were collected
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated in vacuo
10. customThe crude product was purified by chromatography
11. washeluting with 2:1 isohexane
12. customdiethyl ether to yield a highly crystalline solid which