Reaction #317365

Reaction equation

4-Chloro-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine

Triethylamine

(S)-1-Amino-propan-2-ol

→

(R)-1-[6-Methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol

Yield 107.4%

Solvents

THF

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 64 hours
2. 2
   OtherThe reaction mixture was quenched by addition to water
3. 3
   Otherwas partitioned between water and ethyl acetate
4. 4
   OtherThe organic layer was separated
5. 5
   Dryingdried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated under reduced pressure

Procedure

4-Chloro-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine (391 mg, 1.182 mmol) was dissolved in 5 mL of dry THF. Triethylamine (239 mg, 2.363 mmol) was added, and the reaction mixture was stirred for four hours. (S)-1-Amino-propan-2-ol (93 mg, 1.241 mmol) was then added, and the reaction mixture was stirred for 64 hours. The reaction mixture was quenched by addition to water, and was partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered, and evaporated under reduced pressure to give (R)-1-[6-Methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol (469 mg). Mass Spec. M+H=370.

Source