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

HRID 604941Notes

Reaction equation

HRID 604941 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.O>C(N(CC)CC)C.O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:9]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8119AzepaneHCID 775312,4-Dichloropyrimidine

Product 1

HCID 151757481-(2-Chloropyrimidin-4-yl)azepaneYield 20.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2,4-dichloropyrimidine (25 g) in triethylamine (47 mL) and tetrahydrofuran (300 mL) was added azepane (17 g) at 0° C. After returning to room temperature, the solution was stirred for 1 hour. Water was added to thereto and the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:5→1:2) to give the title compound (7.25 g) having the following physical data.

Workup

  1. customAfter returning to room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:5→1:2)

Sources & evidence

ORD record
ord-32a377f2919642238efd708abb2d79d5
Source dataset
uspto-grants-2011_03
Patent number
US07910741B2

Reaction notes

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