3-Pentanamine → HCID 58015804, compound

HRID 2189274Notes

Reaction equation

HRID 2189274 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.[CH2:12]([CH:14]([NH2:17])[CH2:15][CH3:16])[CH3:13].CCN(C(C)C)C(C)C>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][CH:14]([CH2:15][CH3:16])[CH2:12][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 120193-PentanamineHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 58015804HCID 58015804, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloro-5-nitro-pyrimidine (2 g, 10.31 mmol) in anhydrous EtOH (20 ml) is added 1-ethylpropylamine (1.322 ml, 11.341 mmol) at 0 C (ice bath) under inert atmosphere. To this is added neat DIPEA (2.694 ml, 15.465 mmol). The reaction is stirred at r.t. for 8 hrs. The reaction mixture was concentrated in vacuo and the residue is dissolved with EtOAc. The organic layer is washed with sat. NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo. Purification with column chromatography (SiO2, 1:3 EtOAC/Hexane) gives the desired product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue is dissolved with EtOAc
  3. washThe organic layer is washed with sat. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification with column chromatography (SiO2, 1:3 EtOAC/Hexane)

Sources & evidence

ORD record
ord-8287a431d3ea4cd49f59e58d1156b8fc
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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