3-Pentanamine → HCID 58015804, compound

HRID 2189337Notes

Reaction equation

HRID 2189337 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].C(N(CC)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, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloro-5-nitro-pyrimidine (2 g, 10.3 mmol) in anhydrous EtOH (20 mL) is added 1-ethylpropylamine (1.3 mL, 11.3 mmol) and N,N-diisopropylethylamine (2.7 mL, 15.5 mmol) at 0° C. The reaction mixture is stirred for 8 h and concentrated in vacuo. The residue is dissolved with EtOAc, washed with saturated NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo. Purification with column chromatography (SiO2, EtOAC/Hexane 1:3) gives 1.5 g of (2-chloro-5-nitro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved with EtOAc
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification with column chromatography (SiO2, EtOAC/Hexane 1:3)

Sources & evidence

ORD record
ord-d0d111b450d84615bde4c2112c3aa5fd
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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