Reaction #1251

Reaction equation

product

N-Propyl-2,5-dimethyl-3-(2,4,6-trimethylphenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-amine

KOH

1-bromopropane

→

title compound

N,N-Dipropyl-2,5-dimethyl-3-(2,4,6-trimethylphenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-amine

Solvents

DMSO

Conditions

Workup

1. 1
   OtherThe excess bromopropane was then evaporated
2. 2
   OtherThe mixture was partitioned between water and ether
3. 3
   OtherThe aqueous layer was separated
4. 4
   Extractionextracted with ether
5. 5
   WashThe combined ether extracts were washed with water and brine
6. 6
   Dryingdried over Na2SO4
7. 7
   Concentrationconcentrated to an oil
8. 8
   OtherThe oil was purified through silica gel column chromatography

Procedure

A mixture of the product of step F (400 mg, 1.2 mmol), powder KOH (1.0 g) and 1-bromopropane (1 mL) in 2 mL of DMSO was heated at 60° C. for 8 hours. The excess bromopropane was then evaporated. The mixture was partitioned between water and ether. The aqueous layer was separated and extracted with ether. The combined ether extracts were washed with water and brine, dried over Na2SO4 and concentrated to an oil. The oil was purified through silica gel column chromatography to give 260 mg of the title compound as an oil. 1H NMR (CDCl3): d 0.97 (t, 6H), 1.76 (m, 4H), 1.96 (s, 6H), 2.32 (s, 3H), 2.45 (s, 3H), 3.77 (s, 3H), 3.40-4.30 (br, 4H), 6.95 (s, 2H)ppm. The hydrochloride salt prepared in Ether/HCl melted at 210°-13° C.

Source