Reaction #168581

Reaction equation

6-chloropurine

(R)-2-[(E)-2-(3-chlorophenyl)vinyl]-pyrrolidine

triethylamine

→

6-[(R)-2-((E)-2-(3-chlorophenyl)vinyl)pyrrolidin-1-yl]-9H-purine

Yield 16.5%

Solvents

1-butanol

Conditions

Workup

1. 1
   OtherFor work-up, the batch is partitioned between ethyl acetate and water
2. 2
   Dryingthe organic phase is dried over sodium sulfate
3. 3
   Filtrationfiltered off
4. 4
   Otherevaporated in vacuo
5. 5
   OtherThe residue is purified by chromatography

Procedure

695 mg of 6-chloropurine and 850 mg of (R)-2-[(E)-2-(3-chlorophenyl)vinyl]-pyrrolidine are dissolved in 20 ml of 1-butanol and warmed at 130° C. in the microwave for 6 h with 3.1 ml of triethylamine. For work-up, the batch is partitioned between ethyl acetate and water, the organic phase is dried over sodium sulfate, filtered off and evaporated in vacuo. The residue is purified by chromatography, giving 220 mg of 6-[(R)-2-((E)-2-(3-chlorophenyl)vinyl)pyrrolidin-1-yl]-9H-purine (“A11”); Rt: 1.778 min; [M+H]+326.2; m.p. 194-196°;

Source