Water → 1-(2-Chloropyrimidin-4-yl)azepane

HRID 1689838Notes

Reaction equation

HRID 1689838 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[NH:16]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:16]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8119AzepaneHCID 8471TriethylamineHCID 775312,4-Dichloropyrimidine

Product 1

HCID 151757481-(2-Chloropyrimidin-4-yl)azepane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloropyrimidine (3.0 g) in tetrahydrofuran (50 mL) were added triethylamine (4.2 mL) and perhydroazepine (2.5 mL) with ice cooling and the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added water (30 mL) and the resulting mixture was concentrated. The residue was extracted with methylene chloride three times. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1→2:1) to give the title compound (3.03 g) having the following physical data.

Workup

  1. concentrationthe resulting mixture was concentrated
  2. extractionThe residue was extracted with methylene chloride three times
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1→2:1)

Sources & evidence

ORD record
ord-57f91c5ac9b74fcc84441b2299f8844f
Source dataset
uspto-grants-2012_04
Patent number
US08153625B2

Reaction notes

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