Phosphorus pentachloride → 8-(4-Benzyloxy-phenyl)-2-chloro-1-propyl-1,7-dihydro-purin-6-one

HRID 925536Notes

Reaction equation

HRID 925536 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](=O)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:31]>P(Cl)(Cl)(Cl)=O>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[NH:13][C:3]3[C:4](=[O:12])[N:5]([CH2:9][CH2:10][CH3:11])[C:6]([Cl:31])=[N:7][C:2]=3[N:1]=2)=[CH:16][CH:17]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 67133662N-(6-Amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-benzyloxy-benzamide

Product 1

HCID 674964518-(4-Benzyloxy-phenyl)-2-chloro-1-propyl-1,7-dihydro-purin-6-oneYield 30.2%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

The above N-(6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-benzyloxy-benzamide (1.0 g, 0.0025 mol) and phosphorous pentachloride (0.64 g, 0.0025 mol) were taken in phosphorous oxy chloride (25 ml) and refluxed for 20 hours The mixture was cooled and solvent was removed. The residue was dissolved in water (20 ml) and extracted with DCM. (3×5 ml). The organic layer was washed with sat. NaHCO3 (30 ml) followed by saturated brine solution (2×30 ml) and dried over Na2SO4. Solvent was removed and the residue was further purified by column chromatography to obtain pure 8-(4-benzyloxy-phenyl)-2-chloro-1-propyl-1,7-dihydro-purin-6-one (0.298 g, 30%) as a yellow solid.

Workup

  1. temperaturerefluxed for 20 hours The mixture
  2. temperaturewas cooled
  3. customsolvent was removed
  4. dissolutionThe residue was dissolved in water (20 ml)
  5. extractionextracted with DCM
  6. washThe organic layer was washed with sat. NaHCO3 (30 ml)
  7. dry with materialdried over Na2SO4
  8. customSolvent was removed
  9. customthe residue was further purified by column chromatography

Sources & evidence

ORD record
ord-e5cf231a0ca448ba893247f5d4b34d54
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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