Phosphorus oxychloride → 6-Bromo-4-chloro-2-(methylsulfanyl)quinazoline

HRID 1774126Notes

Reaction equation

HRID 1774126 reaction equation
C(N(C(C)C)CC)(C)C.[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([S:21][CH3:22])[N:15]=[C:14]2O.O=P(Cl)(Cl)[Cl:26]>>[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([S:21][CH3:22])[N:15]=[C:14]2[Cl:26]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178503515HCID 178503515, compound

Product 1

HCID 579588116-Bromo-4-chloro-2-(methylsulfanyl)quinazoline

Procedure

Diisopropylethylamine (0.65 ml, 3.69 mmol) was added to a suspension of 6-bromo-2-(methylthio)-quinazolin-4-ol (500 mg, 1.85 mmol) in POCl3 (6.5 ml). The reaction was heated at reflux for 6 hours and then cooled to room temperature. The POCl3 was removed under reduced pressure. The residue was diluted with EtOAc (30 ml) and poured onto ice. The organic layer was washed twice with brine (2×30 ml), then dried over sodium sulfate and concentrated. The product thus obtained was used without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 6 hours
  3. customThe POCl3 was removed under reduced pressure
  4. additionThe residue was diluted with EtOAc (30 ml)
  5. additionpoured onto ice
  6. washThe organic layer was washed twice with brine (2×30 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe product thus obtained
  10. customwas used without further purification

Sources & evidence

ORD record
ord-39ce84942f0c427db04a4d39ef0dd5c7
Source dataset
uspto-grants-2016_02
Patent number
US09259426B2

Reaction notes

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