Potassium Carbonate → 1-[4-(Pyrimidin-2-ylmethoxy)phenyl]-1,2,3,4-tetrahydroquinoxaline

HRID 41689Notes

Reaction equation

HRID 41689 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11](C(O)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:22][C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:24]1[CH:25]=[CH:26][CH:27]=[N:28][C:23]=1[CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 128773712-(Chloromethyl)pyrimidineHCID 668634364-(4-hydroxyphenyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid

Product 1

HCID 668635751-[4-(Pyrimidin-2-ylmethoxy)phenyl]-1,2,3,4-tetrahydroquinoxaline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

0.3 g of the tent-Butyl ester of 4-(4-hydroxyphenyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid is placed in 4.6 ml of dimethylformamide under nitrogen. 0.167 g of 2-(chloromethyl)pyrimidine and 0.508 g of potassium carbonate are added. The reaction medium is heated at 100° C. for 4 h. 0.254 g of potassium carbonate is added and heating is maintained for 1 h 30. After hydrolysis, the reaction medium is extracted with ethyl acetate until the aqueous phase has been completely extracted. The organic phases are combined, washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of methanol in dichloromethane varying from 0% to 9/1. 0.095 g of 1-[4-(pyrimidin-2-ylmethoxy)phenyl]-1,2,3,4-tetrahydro-quinoxaline is obtained.

Workup

  1. temperatureheating
  2. temperatureis maintained for 1 h 30
  3. customAfter hydrolysis
  4. extractionthe reaction medium is extracted with ethyl acetate until the aqueous phase
  5. extractionhas been completely extracted
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated to dryness
  9. customThe crude product obtained
  10. customis chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-333f589f3bbc4ca19acf69b15405d230
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Reaction notes

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