Cyclopentylamine → 2-chloro-N-cyclopentyl-5-nitropyrimidin-4-amine

HRID 1375388Notes

Reaction equation

HRID 1375388 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH:12]1([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 71472532-chloro-N-cyclopentyl-5-nitropyrimidin-4-amineYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.82 g (30 mmol) of 2,4-dichloro-5-nitropyrimidine (N. Whittaker, J. Chem. Soc., 1951:1565–1570) in 100 mL THF at −78° C. is added dropwise over 5 minutes a solution of 5.11 g (60 mmol) of cyclopentylamine in 20 mL THF. After a further 10 minutes at −78° C., the mixture is allowed to warm to room temperature, and the solvent is removed under vacuum. The residue is then extracted into EtOAc, washed with water, and dried with Na2SO4. Removal of the solvent and chromatography on SiO2, eluting with hexane/EtOAc (95:5) gives 6.20 g (85%) of the title compound: mp (hexane) 80–81.5° C.

Workup

  1. customthe solvent is removed under vacuum
  2. extractionThe residue is then extracted into EtOAc
  3. washwashed with water
  4. dry with materialdried with Na2SO4
  5. customRemoval of the solvent and chromatography on SiO2
  6. washeluting with hexane/EtOAc (95:5)

Sources & evidence

ORD record
ord-494382a082364dad9330e3890910adfa
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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