反应详情

温度

-78 °C

Add a freshly prepared solution of lithium di-i-propylamide (150 ml; 62 4 mmol, 0.6 M in THF) to a mixture of 7-(1-ethyl-propyl)-2,5-dimethyl-3-thiazol-5-yl-pyrazolo[1,5-a]pyrimidine, (17.8 g, 62 4 mmol) in THF (100 mL) at −78° C. under a nitrogen atmosphere, keeping the temperature below −74° C. during the addition. Stir the mixture at −78° C. for one hour and then add a solution of N-iodosuccinimide (15 g, 63 mmol) in THF (100 mL) keeping temperature below −74° C. Warm the reaction gradually to 22° C. and then add a 10% aqueous solution of ammonium chloride (300 mL). Separate the organic layer and wash the aqueous layer with methyl-t-butyl ether (2×200 mL). Combine the organic layers, dry over sodium sulfate, filter, and evaporate the solvent. Purify the resulting residue by silica gel chromatography, eluting with hexanes/acetone (5/1) to afford the title compound (15 g, 60%). ES/MS m/z 427 (M+1)+.

1. customthe temperature below −74° C.
2. additionduring the addition
3. customtemperature below −74° C
4. temperatureWarm
5. customthe reaction gradually to 22° C.
6. customSeparate the organic layer
7. washwash the aqueous layer with methyl-t-butyl ether (2×200 mL)
8. dry with materialCombine the organic layers, dry over sodium sulfate
9. filtrationfilter
10. customevaporate the solvent
11. customPurify the resulting residue by silica gel chromatography
12. washeluting with hexanes/acetone (5/1)