Ammonia → HCID 86677080, compound

HRID 1520363Notes

Reaction equation

HRID 1520363 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:16][C:15](=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:3][N:2]=1.N.O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:4]2[CH:5]=[CH:6][N:1]=[N:2][CH:3]=2)[N:16]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 136334002HCID 136334002, compound

Product 1

HCID 86677080HCID 86677080, compound

Conditions

Temperature
0 °C

Procedure

A 100-mL round-bottom flask was charged with 2-(pyridazin-4-yl) quinazolin-4(3H)-one (30 mg) which was suspended in 3 mL of POCl3. The reaction mixture was heated to reflux for 1 h. The reaction mixture turned to a clear brown solution. After cooling, 50 mL of ice/water was carefully added. An aqueous ammonia solution (25% by weight in water) was added dropwise to the mixture with stirring until the pH of the mixture was adjusted to 7˜8. An internal temperature of 0° C. was maintained by the addition of ice. The mixture was warmed to room temperature and extracted with DCM (50 ml×3). The combined organic layers were washed with brine, dried over Na2SO4. After filtration and evaporation, 32 mg was obtained as a light brown solid. LCMS m/z=242.9 (M+1) (Method B) (retention time=1.65 min). The solid was used directly in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. temperatureAfter cooling
  4. temperatureThe mixture was warmed to room temperature
  5. extractionextracted with DCM (50 ml×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration and evaporation
  9. custom32 mg was obtained as a light brown solid
  10. customThe solid was used directly in the next step without further purification

Sources & evidence

ORD record
ord-b069b696a28a4335897602f3dcb238b4
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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