Cyclopentylamine → HCID 59447005, compound

HRID 1946659Notes

Reaction equation

HRID 1946659 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-fb9688f2f066476c8c9a0af76d66739d
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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