Cyclopentylamine → HCID 59447005, compound

HRID 1746643Notes

Reaction equation

HRID 1746643 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:3]=1.[CH:13]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:6]([NH:18][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:7]=1

Participants

6

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylate

Product 1

HCID 59447005HCID 59447005, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A cooled (0° C.) solution of methyl 2,4-dichloropyrimidine-6-carboxylate (Apollo, OR2558, 4.50 g; 21.7 mmol) in anhydrous THF (200 mL) was treated with a solution of cyclopentylamine (Aldrich, 2.36 mL; 23.9 mmol) and triethylamine (3.03 mL; 21.7 mmol) in DCM (60 mL). The reaction mixture was stirred for 1 h30. The organic solvent was removed in vacuo and the crude was redissolved in EtOAc then washed with water and brine. The organic extracts were dried over magnesium sulfate, filtered and concentrated to obtain the crude product, which was purified by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc. The title product was obtained as a white solid.

Workup

  1. customThe organic solvent was removed in vacuo
  2. dissolutionthe crude was redissolved in EtOAc
  3. washthen washed with water and brine
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain the crude product, which
  8. customwas purified by column chromatography (silica)
  9. washeluting with cyclohexane containing
  10. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-477c91bc52474642af2f2b37bd3f430e
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

Loading…