Sodium Carbonate → 4-(6-Chloropyrimidin-4-yl)-1,4-oxazepane

HRID 562458Notes

Reaction equation

HRID 562458 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.Cl.[O:10]1[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:13]2[CH2:14][CH2:15][CH2:16][O:10][CH2:11][CH2:12]2)[CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 709434,6-DichloropyrimidineHCID 230902141,4-Oxazepane hydrochloride

Product 1

HCID 579250744-(6-Chloropyrimidin-4-yl)-1,4-oxazepane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0 g (20.1 mmol) of 4,6-dichloropyrimidine, 2.8 g (20.1 mmol) of 1,4-oxazepane hydrochloride and 6.4 g (60.4 mmol) of sodium carbonate in 45 ml of water is stirred under reflux for 16 h. After cooling to RT, the reaction mixture is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate and filtered. Under reduced pressure, the filtrate is concentrated to dryness. The product is obtained as an oil. Yield: 3.9 g (86% of theory)

Workup

  1. temperatureunder reflux for 16 h
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationUnder reduced pressure, the filtrate is concentrated to dryness
  7. customThe product is obtained as an oil

Sources & evidence

ORD record
ord-02114a0da9974209a1d6ddd9523d55b9
Source dataset
uspto-grants-2011_11
Patent number
US08067407B2

Reaction notes

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