Phosphorus oxychloride → HCID 21075023, compound

HRID 351418Notes

Reaction equation

HRID 351418 reaction equation
[C:1]([C:5]1[N:6]=[CH:7][C:8]2[N:9]=[CH:10][N:11]=[C:12](O)[C:13]=2[N:14]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:18])=O>>[C:1]([C:5]1[N:6]=[CH:7][C:8]2[N:9]=[CH:10][N:11]=[C:12]([Cl:18])[C:13]=2[N:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178441595HCID 178441595, compound

Product 1

HCID 21075023HCID 21075023, compound

Procedure

6-tert-Butyl-pyrimido[5,4-d]pyrimidin-4-ol (210 mg, 1.03 mMol) was dissolved in phosphorous oxychloride (10 mL), and the mixture was heated at reflux for 4 hours. The solution was concentrated in-vacuo, then stripped from methylene chloride (3×50 mL) to remove excess phosphorous oxychloride. The residue was stirred for 10 minutes in saturated sodium bicarbonate (50 mL), then extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with water (30 mL), followed by brine (30 mL), dried over sodium sulfate, then concentrated in-vacuo. The residue was purified over silica gel, eluting with 50% ethyl acetate/heptane, to yield 150 mg of a white solid as product. NMR (500 MHz, CDCl3) δ 9.61 (s, 1H), 9.15 (S, 1H), 1.52 (s, 9H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. concentrationThe solution was concentrated in-vacuo
  4. customto remove excess phosphorous oxychloride
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. washThe combined organic phases were washed with water (30 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in-vacuo
  9. customThe residue was purified over silica gel
  10. washeluting with 50% ethyl acetate/heptane

Sources & evidence

ORD record
ord-6336552a89fa4f2db98cce655dd475dd
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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