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

HRID 2039481Notes

Reaction equation

HRID 2039481 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-ec22e14b7acc48e89d69003ca983711d
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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