Sodium hydride → 4-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine

4-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine (10.0 g, 0.032 mol) was added to 100 mL of dry DMF, and the resulting solution was cooled to 0° C. (2-Chloromethoxy-ethyl)-trimethyl-silane (6.8 mL, 0.038 mol) was added dropwise, and the reaction mixture was stirred for five minutes. Sodium hydride (1.40 g, 0.0333 mol) was then added, and the reaction mixture was stirred for 30 minutes at 0° C. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated, and the aqueous layer was washed twice with ethyl acetate. The combined organic layers were washed with brine, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (0% to 10% hexanes in EtOAc) to afford 8.55 g of 4-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine.

1. additionwas added dropwise
2. stirringthe reaction mixture was stirred for 30 minutes at 0° C
3. customThe reaction mixture was partitioned between water and ethyl acetate
4. customThe layers were separated
5. washthe aqueous layer was washed twice with ethyl acetate
6. washThe combined organic layers were washed with brine
7. washwashed with water
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by flash chromatography (0% to 10% hexanes in EtOAc)

ORD record

ord-ac6ef403bbd341f398398dc308a047a8

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07435731B2