Cyclopentylamine → HCID 23356634, compound

HRID 233575Notes

Reaction equation

HRID 233575 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6](Cl)[N:5]2[N:16]=[CH:17][N:18]=[C:4]2[N:3]=1.[CH:19]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6]([NH:24][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[N:5]2[N:16]=[CH:17][N:18]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 11108687HCID 11108687, compound

Product 1

HCID 23356634HCID 23356634, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5,7 Dichloro-6-(4-methylphenyl)-1,2,4-triazolo-[1,5-a]pyrimidine (1.8 g, 6 mmol) was dissolved in tetrahydrofuran. A solution of cyclopentylamine (0.51 g, 6 mmol) and triethylamine (0.61 g, 6 mmol) in tetrahydrofuran (2 ml) was then added with stirring and the stirring continued for a further 3 hours at ambient temperature (20° C.). The reaction mixture was then evaporated in vacuo and the residue extracted with dichloromethane and water (100 ml each). The organic layer was dried over sodium sulphate and the solvent evaporated in vacuo. The residue was crystallized from ethyl acetate to give 1.7 g 5-chloro-6-(4-methylphenyl)-7-cyclopentylamino-1,2,4-triazolo[1,5-a]pyrimidine as yellowish crystals, m.pt. 158° C. Yield: 87% of theoretical 1H-NMR: δ=1.3-1.75 (2 m, 8H); 2.43(s,1H); 3.73 (m,1H); 5.97 (d,1H); 7.25 (m,4H); 8.25(s,1H) ppm

Workup

  1. custom(20° C.)
  2. customThe reaction mixture was then evaporated in vacuo
  3. extractionthe residue extracted with dichloromethane and water (100 ml each)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customthe solvent evaporated in vacuo
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-5638d26290b74d7b8895957b9209c089
Source dataset
uspto-grants-1997_01
Patent number
US05593996

Reaction notes

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