Water → [6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-carbamic acid ethyl ester

HRID 1020070

Reaction equation

HRID 1020070 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][CH2:24][O:25][CH:26]=[O:27].O>CC(=O)CC>[CH2:24]([O:25][C:26](=[O:27])[NH:15][C:11]1[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[N:14]=[CH:13][N:12]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2467482-Chloroethyl formateHCID 49758439HCID 49758439, compound

Product 1

HCID 59509103[6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-carbamic acid ethyl esterYield 44.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (1.0 g, 4.9 mmol) and potassium carbonate (4.0 g, 29 mmol) in 2-butanone (10 ml), chloroethylformate (0.50 ml, 4.9 mmol) was added and the mixture was refluxed for 3 hours at 80° C. The reaction was monitored by TLC. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to provide 0.60 g of [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-carbamic acid ethyl ester (XL).

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-df3a111454854ef9aba1f62402650947
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Linked notes

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