Phosphorus oxychloride → HCID 23070627, compound

HRID 501383Notes

Reaction equation

HRID 501383 reaction equation
[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10](=O)[NH:9][C:8]=2[N:7]=[C:6]1[N:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)[C:2]#[C:3][CH3:4].P(Cl)(Cl)([Cl:39])=O>>[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]([Cl:39])=[N:9][C:8]=2[N:7]=[C:6]1[N:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)[C:2]#[C:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 23070881HCID 23070881, compound

Product 1

HCID 23070627HCID 23070627, compound

Conditions

Temperature
120 °C

Procedure

A mixture consisting of 290 mg of t-butyl 4-[7-(2-butynyl)-2,6-dioxo-1-(2-phenylethyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylate and 4 ml of phosphorus oxychloride was heated and stirred in an oil bath at 120° C. for 8 hours. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in 5 ml of tetrahydrofuran. This solution was added dropwise to a mixture consisting of 250 mg of di-t-butyl dicarbonate, 10 ml of a saturated sodium bicarbonate solution, and 10 ml of tetrahydrofuran while the mixture was being stirred and cooled with ice. The mixture was incubated at room temperature for 4 hours, and then extracted with ethyl acetate. The organic layer was washed with water then with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduce pressure. The residue was purified by silica gel column chromatography using 30 to 50% ethyl acetate/hexane. Then, the material was further purified by reverse-phase column chromatography using 50 to 100% methanol/water to give 60 mg of the title compound.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 5 ml of tetrahydrofuran
  4. additionThis solution was added dropwise to a mixture
  5. stirringwas being stirred
  6. temperaturecooled with ice
  7. waitThe mixture was incubated at room temperature for 4 hours
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with water
  10. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel column chromatography
  13. customThen, the material was further purified by reverse-phase column chromatography

Sources & evidence

ORD record
ord-88d398d26d444459bd604a520f699f3d
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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