Phosphorus oxychloride → HCID 86036625, compound

HRID 2225183Notes

Reaction equation

HRID 2225183 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][N:11]=[C:10]2O.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:10]1[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:8]=2)[N:13]=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517958HCID 178517958, compound

Product 1

HCID 86036625HCID 86036625, compound

Procedure

Preparation D12, Step 3: A suspension of 6-(pyridin-2-yl)quinazolin-4-ol (106 mg, 0.47 mmol) in phosphorous oxychloride (15 mL) was heated at reflux for 1.5 h, during which time a clear, amber solution was observed. The solution was cooled to room temperature, concentrated in-vacuo, and stripped 2× from 30 mL methylene chloride to remove any remaining phosphorous oxychloride. The residue was partitioned between EtOAc and saturated sodium bicarbonate, and the mixture was stirred for 10 min. The layers were separated, and the organic phase was washed successively with saturated sodium bicarbonate, water, and brine, dried over sodium sulfate, then concentrated in-vacuo. The residue was purified over silica gel, eluting with methylene chloride followed by 1:1 methylene chloride/EtOAc, to yield 105 mg of 4-chloro-6-(pyridin-2-yl)quinazoline as a white solid. MS (ES+)=242 (M+H+).

Workup

  1. customPreparation D12, Step 3
  2. temperaturewas heated
  3. temperatureat reflux for 1.5 h, during which time a clear, amber solution
  4. concentrationconcentrated in-vacuo
  5. customto remove any remaining phosphorous oxychloride
  6. customThe residue was partitioned between EtOAc and saturated sodium bicarbonate
  7. customThe layers were separated
  8. washthe organic phase was washed successively with saturated sodium bicarbonate, water, and brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in-vacuo
  11. customThe residue was purified over silica gel
  12. washeluting with methylene chloride

Sources & evidence

ORD record
ord-a72bcd36637f4af59b4e83121a54f721
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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