Phosphorus pentachloride → HCID 69937333, compound

HRID 2401307Notes

Reaction equation

HRID 2401307 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=O)[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[C:3]=1[NH:13][C:14]([CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=O.P(Cl)(Cl)(Cl)(Cl)[Cl:22]>P(Cl)(Cl)(Cl)=O>[CH:16]1([C:14]2[NH:13][C:3]3[C:4](=[O:12])[N:5]([CH2:9][CH2:10][CH3:11])[C:6]([Cl:22])=[N:7][C:2]=3[N:1]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 14978323HCID 14978323, compound

Product 1

HCID 69937333HCID 69937333, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

To a suspension of cyclopentanecarboxylic acid (6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (0.40 g, crude) obtained from step 1 in phosphorus oxychloride (25 ml) was added phosphorus pentachloride (0.10 g) and the resulting reaction mixture was refluxed overnight. Phosphorus oxychloride was evaporated under reduced pressure. The residue was slowly quenched with water. Ethyl acetate was added and the organic layer was separated and washed thoroughly with water followed by brine. The ethyl acetate layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by preparative TLC using dichloromethane, methanol (9:1) as the solvent system to give 0.075 g (19% over two steps) of the product as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. customPhosphorus oxychloride was evaporated under reduced pressure
  4. customThe residue was slowly quenched with water
  5. additionEthyl acetate was added
  6. customthe organic layer was separated
  7. washwashed thoroughly with water
  8. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
  9. concentrationconcentrated under vacuum
  10. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-690ae2856deb4856aaa758cf170276a7
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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