Reaction #317380

Reaction equation

4-Chloro-3-cyclopentyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine

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

→

(R)-1-(3-Cyclopentyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)-propan-2-ol

Yield 97.9%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated
2. 2
   Temperatureto reflux for three hours
3. 3
   OtherThe reaction mixture was partitioned between water and ethyl acetate
4. 4
   Otherthe organic phase was separated
5. 5
   Washwashed with water
6. 6
   Washwashed with brine
7. 7
   Dryingdried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated under reduced pressure

Procedure

4-Chloro-3-cyclopentyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine (500 mg, 1.860 mmol) was dissolved in 25 mL dry THF, and (S)-1-Amino-propan-2-ol (1.758 mL, 22.32 mmol) was added. The reaction mixture was heated to reflux for three hours, then cooled to room temperature. The reaction mixture was partitioned between water and ethyl acetate, and the organic phase was separated, washed with water, washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to give 0.56 g of (R)-1-(3-Cyclopentyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)-propan-2-ol. Mass Spec. M+H=309.

Source