4-Fluoroaniline → HCID 66882957, compound

HRID 880126Notes

Reaction equation

HRID 880126 reaction equation
C[Al](C)C.[CH2:5]([N:7]1[C:12](=[O:13])[CH:11]=[C:10]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:9]=[C:8]1[CH2:20][C:21]([O:23]CC)=O)[CH3:6].[F:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1.S([O-])([O-])(=O)=O.[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH2:5]([N:7]1[C:12](=[O:13])[CH:11]=[C:10]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[N:9]=[C:8]1[CH2:20][C:21]([NH:31][C:30]1[CH:32]=[CH:33][C:27]([F:26])=[CH:28][CH:29]=1)=[O:23])[CH3:6]

Participants

8

Reactant 4

HCID 97314-FluoroanilineHCID 24507Potassium SulfateHCID 16682925TrimethylaluminumHCID 70807095HCID 70807095, compound

Product 1

HCID 66882957HCID 66882957, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

0.640 ml of a 2M solution of trimethylaluminium in toluene, and then, after stirring for 40 minutes at ambient temperature, a solution of 190 mg of ethyl [1-ethyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate in 6 ml of toluene are successively added, dropwise, to a solution of 0.13 ml of 4-fluoroaniline in 4 ml of toluene. The reaction mixture is heated at 80° C. for 4 hours, cooled using an ice bath and run into water. A 1M solution of potassium sulphate and ethyl acetate are then added, and the organic phase is extracted, washed again with a 1M solution of potassium phosphate and then dried over magnesium phosphate, filtered and, finally, concentrated under reduced pressure. After purification by silica column chromatography, eluent: 980101 then 960202 CH2Cl2/CH3CN/MeOH, 60 mg of 2-[1-ethyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]-N-(4-fluorophenyl)acetamide are obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. temperaturecooled
  2. extractionthe organic phase is extracted
  3. washwashed again with a 1M solution of potassium phosphate
  4. dry with materialdried over magnesium phosphate
  5. filtrationfiltered
  6. concentrationfinally, concentrated under reduced pressure
  7. customAfter purification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-1ac2928766fd4f6b8d40aecdf9e1e55e
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

Loading…