Phosphorus oxychloride → HCID 23020409, compound

HRID 747152Notes

Reaction equation

HRID 747152 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=O)[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:3]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:6]1[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135546394HCID 135546394, compound

Product 1

HCID 23020409HCID 23020409, compoundYield 48%

Conditions

Temperature
100 °C

Procedure

A suspension of 2-amino-6-(3-fluorophenyl)-5-(4-pyridyl)-3,4-dihydro-4-pyrimidinone (1.0 g, 3.54 mmol) in phosphorus oxychloride (15 ml) was stirred at 100° C. for 30 minutes under an atmosphere of nitrogen gas. After cooling as it was, the reaction mixture was concentrated and the residue was dissolved in ethyl acetate and 2N sodium hydroxide. The organic layer was washed with an aqueous saturated sodium bicarbonate solution twice and brine, dried over anhydrous sodium sulfate and concentrated. To the residue was added diethyl ether, and the resulting precipitates were collected by filtration and washed with diethyl ether, to give the title compound (513 mg, 48%) as a colorless solid.

Workup

  1. temperatureAfter cooling as it
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution twice
  5. dry with materialbrine, dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. additionTo the residue was added diethyl ether
  8. customthe resulting precipitates
  9. filtrationwere collected by filtration
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-5604a566e18f4d3dbe5b7291ee0e653f
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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