Triethylamine → HCID 178478083, compound

HRID 81399Notes

Reaction equation

HRID 81399 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[Cl:11][C:12]1[CH:13]=[C:14](/[CH:18]=[CH:19]/[C@H:20]2[CH2:24][CH2:23][CH2:22][NH:21]2)[CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>C(O)CCC>[Cl:11][C:12]1[CH:13]=[C:14](/[CH:18]=[CH:19]/[C@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53592776-ChloropurineHCID 67017467HCID 67017467, compound

Product 1

HCID 178478083HCID 178478083, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

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°;

Workup

  1. customFor work-up, the batch is partitioned between ethyl acetate and water
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. filtrationfiltered off
  4. customevaporated in vacuo
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-20b573977b3d429abda11f3a2d0ef818
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Reaction notes

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