Ammonia → 4-Chloro-6-phenylfuro[2,3-d]pyrimidine

HRID 1926866Notes

Reaction equation

HRID 1926866 reaction equation
[C:1]1([C:7]2[O:16][C:10]3[N:11]=[CH:12][NH:13][C:14](=O)[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:19])=O.Cl.N>O>[Cl:19][C:14]1[C:9]2[CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:16][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 580167996-phenylfuro[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 579464884-Chloro-6-phenylfuro[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Suspend 50 g (235.6 mmol) 6-phenylfuro[2,3-d]pyrimidin-4(3H)-one at RT in 375 ml (4023 mmol) phosphoryl chloride and heat the mixture to boiling (evolution of HCl). After 1 h, cool the dark solution to RT and add dropwise to a vigorously stirred mixture of 1.25 litre water and 2.25 litre conc. ammonia solution (25 wt. %) (heating to 55-75° C., pH>9). At the end of addition, cool to RT and extract the mixture three times with 1.6 litre dichloromethane each time. Combine the organic phases, dry, and concentrate by vacuum evaporation. Stir the residue with diethyl ether, filter with suction, and dry at high vacuum. 47.3 g (87% of theor.) of the target compound is obtained.

Workup

  1. customat RT
  2. temperatureheat the mixture
  3. additionAt the end of addition
  4. temperaturecool to RT
  5. extractionextract the mixture three times with 1.6 litre dichloromethane each time
  6. customdry
  7. concentrationconcentrate by vacuum evaporation
  8. filtrationfilter with suction
  9. customdry at high vacuum
  10. custom47.3 g (87% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-e4fe06c649284a7da85cd9a848f313a8
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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