Ammonia → 4-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

HRID 2189024Notes

Reaction equation

HRID 2189024 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16](=O)[NH:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:27])=O.Cl.N>O>[Cl:27][C:16]1[C:17]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:11][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 58016809HCID 58016809, compound

Product 1

HCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Suspend 135 g (424 mmol) 5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4(3H)-one at RT in 675 ml (7241 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 2.25 liter water and 4.05 liter 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 1.0 liter 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. 134.4 g (94.1% of theor.) of the title 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 1.0 liter dichloromethane each time
  6. customdry
  7. concentrationconcentrate by vacuum evaporation
  8. filtrationfilter with suction
  9. customdry at high vacuum

Sources & evidence

ORD record
ord-14cbf6bcaa014a04b3f51ad34e4f1f6c
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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