Phosphorus oxychloride → HCID 59362936, compound

HRID 1668808Notes

Reaction equation

HRID 1668808 reaction equation
[CH:1]1([C:6]2[N:11]=[C:10](O)[C:9]3[CH2:13][CH2:14][CH2:15][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:10]1[C:9]2[CH2:13][CH2:14][CH2:15][C:8]=2[N:7]=[C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517420HCID 178517420, compound

Product 1

HCID 59362936HCID 59362936, compoundYield 86%

Procedure

A mixture of 2-cyclopentyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ol (4.5 g, 22 mmol) and phosphorus oxychloride (13 mL, 130 mmol) was heated to reflux for 4 hours. Thereafter, volatiles were evaporated under reduced pressure and the mixture was poured over ice-water. After stirring for 1 hour, the product was extracted with dichloromethane (3×50 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 (4.2 g, 86% yield)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customThereafter, volatiles were evaporated under reduced pressure
  4. additionthe mixture was poured over ice-water
  5. extractionthe product was extracted with dichloromethane (3×50 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-43120d9f15e241e4b8d973c40b3626e9
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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