Water → 1-Acetyl-4-(4,6-difluoropyrimidin-2-yl)piperazine

HRID 1282153Notes

Reaction equation

HRID 1282153 reaction equation
[F:1][C:2]1[N:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:16]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)(=[O:18])[CH3:17].O>C(#N)C>[C:16]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[N:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[N:3]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17].[C:16]([N:19]1[CH2:24][CH2:23][N:22]([C:6]2[CH:5]=[C:4]([F:9])[N:3]=[C:2]([F:1])[N:7]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 696772,4,6-TrifluoropyrimidineHCID 837951-Acetylpiperazine

Product 2

HCID 184230501-Acetyl-4-(4,6-difluoropyrimidin-2-yl)piperazineHCID 184231521-Acetyl-4-(2,6-difluoropyrimidin-4-yl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2,4,6-trifluoropyrimidine (2.0 g) and potassium carbonate (3.1 g) in acetonitrile (15 ml) was added a solution of 1-acetylpiperazine (1.9 g) in acetonitrile (5 ml) over 10 min under ice-cooling and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-yellow oil. The obtained pale-yellow oil was purified by silica gel column chromatography to give the title compound (1.8 g) and 1-acetyl-4-(2,6-difluoropyrimidin-4-yl)piperazine (1.7 g) both as a white solid.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give a pale-yellow oil
  7. customThe obtained pale-yellow oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b2048bc1cd7a4f399b5faa32651e1386
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

Loading…