Phosphorus oxychloride → HCID 86677068, compound

HRID 1520310Notes

Reaction equation

HRID 1520310 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]=[C:7]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[N:6]=[C:5]2O.P(Cl)(Cl)([Cl:22])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]=[C:7]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[N:6]=[C:5]2[Cl:22]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517518HCID 178517518, compound

Product 1

HCID 86677068HCID 86677068, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 6-bromo-8-fluoro-2-(pyridin-3-yl)quinazolin-4-ol (6.16 g, 0.0192 mol) in toluene (60 mL) was added phosphorus oxychloride (5.30 ml, 0.0579 mol) at room temperature. The mixture was refluxed for 3 h. The solvent was evaporated and water was added to the residue under cooling conditions. The suspension was stirred at room temperature for 30 min, the resulting precipitate was filtered and dried to give the title compound (6.5 g, quantitative). 1H NMR (400 MHz, DMSO) δ 9.58 (d, J=1.6 Hz, 1H), 8.82 (dd, J=4.7, 1.5 Hz, 1H), 8.80-8.75 (m, 1H), 8.37 (dd, J=9.7, 1.9 Hz, 1H), 8.34-8.29 (m, 1H), 767 (dd, J=7.8, 4.6 Hz, 1H).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe solvent was evaporated
  3. additionwater was added to the residue under cooling conditions
  4. filtrationthe resulting precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-38faf92fc6a847a58779d792cdbd5cf7
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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