Water → HCID 61146104, compound

HRID 576076Notes

Reaction equation

HRID 576076 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[C:18]1([CH2:24][CH2:25][CH2:26][NH2:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>O1CCCC1>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([NH:27][CH2:26][CH2:25][CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:7][CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 162593-PhenylpropylamineHCID 825442-Chloro-5-nitropyrimidine

Product 1

HCID 61146104HCID 61146104, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-5-nitropyrimidine (100 mg, 0.627 mmol) and triethylamine (96 μL, 0.690 mmol) were added successively to a solution of 3-phenylpropylamine (98 μL, 0.690 mmol) in tetrahydrofuran, and the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and 0.5 mol/L hydrochloric acid and dried over anhydrous magnesium sulfate. Thereafter, the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to afford 5-nitro-N-(3-phenylpropyl)pyrimidin-2-amine as a colorless solid (108 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine and 0.5 mol/L hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThereafter, the desiccant was filtered off
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-b806af82f2304f21ae51a20c1e6387b1
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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