Reaction #8682

Reaction equation

water

sodium carbonate

3-[5-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2-pyrimidinyl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

2-iodopropane

→

1-(2-Fluorobenzyl)-3-[5-(5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-2-pyrimidinyl]-1H-pyrazol[3,4-b]pyridine

Solvents

acetone

Conditions

Workup

1. 1
   Extractionextracted with DCM
2. 2
   Washwashed with saturated aqueous sodium chloride solution
3. 3
   Otherdried
4. 4
   Filtrationfiltered
5. 5
   OtherThe solvent is removed in vacuo
6. 6
   Otherthe residue is purified by preparative HPLC with addition of small portions of aqueous hydrochloric acid
7. 7
   Other25 mg (42% of theory) of the product are obtained

Procedure

50 mg (0.13 mmol) of 3-[5-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2-pyrimidinyl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine (example 9) are dissolved in 5 ml of absolute acetone, and 92 mg (0.87 mmol) of sodium carbonate are added. 64 mg (0.37 mmol) of 2-iodopropane are added to the suspension, and the mixture is stirred at RT overnight. The reaction solution is mixed with water and extracted with DCM. The organic phases are combined, washed with saturated aqueous sodium chloride solution, dried and filtered. The solvent is removed in vacuo, and the residue is purified by preparative HPLC with addition of small portions of aqueous hydrochloric acid. 25 mg (42% of theory) of the product are obtained.

Source