Reaction #7701

Reaction equation

(2-chloroquinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine

benzylmagnesium chloride

→

(2-benzyl-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine

Solvents

THF

THF

Conditions

Workup

1. 1
   Otherthe reaction mixture is then quenched with aqueous NH4Cl
2. 2
   Extractionthe product extracted in ethyl acetate
3. 3
   OtherThe solvent is evaporated
4. 4
   Otherthe residue purified by flash chromatography

Procedure

To a solution of the above-prepared (2-chloroquinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (123 mg, 0.43 mmol) in THF (5 mL) is added NiCl2(dppp) (12 mg, 2.1.10−5 mol), followed by 1M benzylmagnesium chloride in THF (2.15 mL, 2.15 mmol). The solution is heated at 50° C. for 20 hours and the reaction mixture is then quenched with aqueous NH4Cl and the product extracted in ethyl acetate. The solvent is evaporated and the residue purified by flash chromatography to yield the desired (2-benzyl-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine.

Source