Cyclopentylamine → HCID 18914309, compound

HRID 1292089Notes

Reaction equation

HRID 1292089 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)=[C:6](Cl)[N:5]2[N:14]=[CH:15][N:16]=[C:4]2[N:3]=1.[CH:17]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)=[C:6]([NH:22][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:5]2[N:14]=[CH:15][N:16]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 18914308HCID 18914308, compound

Product 1

HCID 18914309HCID 18914309, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5,7-Dichloro-6-thien-3-yl-1,2,4-triazolo[1,5-a]pyrimidine (0.54 g, 0.002 mol) was dissolved in tetrahydrofuran (20 ml). A mixture of cyclopentylamine (0.2 g, 0.002 mol), tetrahydrofuran (2 ml) and triethylamine (0.25 g, 0.002 mol) was then added with stirring and the stirring continued for a further hour after the addition was complete. The solvent was then distilled off in vacuo and the residue treated with ethyl acetate and water (50 ml each). The organic phase was separated, dried with sodium sulphate, filtered and the solvent removed in vacuo. The residue was purified by chromatography on silica gel using 8:2 ethyl acetate: petroleum ether (300 ml) as eluant to give 0.45 g 5-chloro-6-thien-3yl-7-cyclopentylamino-1,2,4-triazolo[1,5-a]-pyrimidine as colourless crystals, m.pt. 78° C. Yield: 71% of theoretical.

Workup

  1. additionwas then added
  2. waitthe stirring continued for a further hour
  3. additionafter the addition
  4. distillationThe solvent was then distilled off in vacuo
  5. additionthe residue treated with ethyl acetate and water (50 ml each)
  6. customThe organic phase was separated
  7. dry with materialdried with sodium sulphate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customThe residue was purified by chromatography on silica gel using 8:2 ethyl acetate

Sources & evidence

ORD record
ord-d1bcde8b256c4d0d992234e9b1564642
Source dataset
uspto-grants-1998_05
Patent number
US05756509

Reaction notes

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