Triethylamine → 4-Chloro-6,7-difluoroquinazoline

HRID 1917627Notes

Reaction equation

HRID 1917627 reaction equation
O=P(Cl)(Cl)[Cl:3].[F:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[F:17])[N:13]=[CH:12][N:11]=[C:10]2O.C(N(CC)CC)C>>[Cl:3][C:10]1[C:9]2[C:14](=[CH:15][C:16]([F:17])=[C:7]([F:6])[CH:8]=2)[N:13]=[CH:12][N:11]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178518023HCID 178518023, compound

Product 1

HCID 210882784-Chloro-6,7-difluoroquinazolineYield 87%

Conditions

Temperature
100 °C

Procedure

To POCl3 (15 mL) was added 6,7-difluoro-4-hydroxyquinazoline (910 mg, 5 mmol) followed by triethylamine (700 uL, 5 mmol). The solution was then heated at 100° C. for 4 hours and concentrated in vacuo. The resulting sludge was triturated with EtOAc (2×100 mL), and the combined decanted org layers were flushed through a plug of silica gel to give 4-chloro-6,7-difluoroquinazoline (870 mg, 4.35 mmol, 87%). LC-MS (ESI) m/z 201 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting sludge was triturated with EtOAc (2×100 mL)
  3. customthe combined decanted org layers
  4. customwere flushed through a plug of silica gel

Sources & evidence

ORD record
ord-c46b6cc0dfc343b99035eb5a5390d58a
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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