Ammonia → 4-Chloro-5-phenylfuro[2,3-d]pyrimidine

HRID 2189027Notes

Reaction equation

HRID 2189027 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]1([C:12]2[C:20]3[C:19](=O)[NH:18][CH:17]=[N:16][C:15]=3[O:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N>O>[Cl:3][C:19]1[C:20]2[C:12]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:13][O:14][C:15]=2[N:16]=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 594278305-phenylfuro[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 594278334-Chloro-5-phenylfuro[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 9.5 ml (101.8 mmol) phosphoryl chloride to 1.8 g (approx. 6.8 mmol) 5-phenylfuro[2,3-d]pyrimidin-4(3H)-one at RT and heat the mixture for 1 h under reflux. Cool the resultant black mixture to RT and carefully add dropwise at <10° C. to a well-stirred solution of 70 ml conc. ammonia solution and 50 ml water cooled to 0° C. (pH>9). At the end of addition, heat the black suspension to RT and stir for a further 15 min. Filter off the black solid with suction, resuspend with water three times, filter with suction again, and dry at high vacuum. Dissolve the solid in dichloromethane and column-filter on silica gel (solvent: dichloromethane). 1371 mg (80.6% of theor.) of the target compound is obtained as a yellow solid.

Workup

  1. temperatureheat the mixture for 1 h
  2. temperatureunder reflux
  3. temperaturecooled to 0° C. (pH>9)
  4. additionAt the end of addition
  5. temperatureheat the black suspension to RT
  6. filtrationFilter off the black solid with suction
  7. filtrationfilter with suction again
  8. customdry at high vacuum
  9. dissolutionDissolve the solid in dichloromethane
  10. filtrationcolumn-filter on silica gel (solvent: dichloromethane)
  11. custom1371 mg (80.6% of theor.) of the target compound is obtained as a yellow solid

Sources & evidence

ORD record
ord-809c333759a840b297bee24be6ec9c1e
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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