Phosphorus oxychloride → HCID 59362951, compound

HRID 1668814Notes

Reaction equation

HRID 1668814 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH:6]1([CH2:11][C:12]2[N:17]=[C:16](O)[C:15]3[CH2:19][CH2:20][CH2:21][C:14]=3[N:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1>>[Cl:3][C:16]1[C:15]2[CH2:19][CH2:20][CH2:21][C:14]=2[N:13]=[C:12]([CH2:11][CH:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[N:17]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517618HCID 178517618, compound

Product 1

HCID 59362951HCID 59362951, compoundYield 78%

Procedure

Phosphorus oxychloride (4.6 mL, 51 mmol) was added to 2-cyclopentylmethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ol (3.7 g, 17 mmol) and the mixture was heated at reflux for 2 hours. Thereafter, volatiles were evaporated under reduced pressure and the mixture was poured over ice-water. The mixture was extracted with dichloromethane (3×60 mL). The combined organic extracts were washed with water, treated with activated charcoal, dried over anhydrous Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a light yellow solid (3.1 g, 78% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customThereafter, volatiles were evaporated under reduced pressure
  4. additionthe mixture was poured over ice-water
  5. extractionThe mixture was extracted with dichloromethane (3×60 mL)
  6. washThe combined organic extracts were washed with water
  7. additiontreated with activated charcoal
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-debfe7ca4f584bcc9ace96b57ebbcc4e
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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