Reaction #2326963

Reaction equation

7-[2-(t-Butyldimethylsilanyloxy)ethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

2-furoic acid hydrazide

→

furan-2-carboxylic acid N′-{2-amino-7-[2-(t-butyldimethylsilanyloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-hydrazide

Solvents

n-butanol

Conditions

Workup

1. 1
   OtherThe solvent is evaporated under vacuum
2. 2
   Otherthe residue is purified by flash chromatography

Procedure

The title A compound, 7-[2-(t-Butyldimethylsilanyloxy)ethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (100 mg, 0.3 mmol) and 2-furoic acid hydrazide (76 mg, 0.6 mmol) are taken into 3 mL of n-butanol. The mixture is stirred at 120° C. under N2 for 2 h. The solvent is evaporated under vacuum and the residue is purified by flash chromatography using EtOAc/MeOH (95/5) as eluent to give furan-2-carboxylic acid N′-{2-amino-7-[2-(t-butyldimethylsilanyloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-hydrazide: LC/MS (M+1=417). 1H NMR (CDCl3, 400 MHz) δ-0.08 (s, 6H), 0.84 (s, 9H), 3.85 (t, 2H, J=4.8 Hz), 4.12 (t, 2H, J =4.8 Hz), 4.81 (br s, 2H, NH2), 6.26 (d, 1H, J=2.4 Hz), 6.51 (m, 1H), 6.74 (d, 1H, J=2.4 Hz), 7.20 (d, 1H, J=2.8 Hz), 7.27 (d, 1H, J=2.8 Hz), 7.49 (s, 1H).

Source