Phosphorus oxychloride → 4-Chloro-6-methyl-5-propylpyrimidine

HRID 898705Notes

Reaction equation

HRID 898705 reaction equation
[CH2:1]([C:4]1[C:5](=O)[NH:6][CH:7]=[N:8][C:9]=1[CH3:10])[CH2:2][CH3:3].O=P(Cl)(Cl)[Cl:14]>>[CH2:1]([C:4]1[C:5]([Cl:14])=[N:6][CH:7]=[N:8][C:9]=1[CH3:10])[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1355027734-Pyrimidinol, 6-methyl-5-propyl-

Product 1

HCID 223131564-Chloro-6-methyl-5-propylpyrimidine

Conditions

Temperature
85 °C

Procedure

A mixture of 5-propyl-6-methyl-pyrimidin4-one (10 mmol) and POCl3 (25 ml) is heated at 85° C. for 4 hours. The solvent is removed in vacuo and EtOAc (30 ml) and water (30 ml) are added to the residue. NaHCO3 is carefully added until the pH of aqueous layer is greater than 7. The layers are separated and the aqueous layer is extracted with EtOAc (2×30 ml). The combined extracts are washed with brine (50 ml), dried (Na2SO4), and evaporated. Flash column purification of the residue with 6:1 EtOAc:hexane provides the title product as a light yellow oil.

Workup

  1. customThe solvent is removed in vacuo and EtOAc (30 ml) and water (30 ml)
  2. additionare added to the residue
  3. additionNaHCO3 is carefully added until the pH of aqueous layer
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with EtOAc (2×30 ml)
  6. washThe combined extracts are washed with brine (50 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customFlash column purification of the residue with 6:1 EtOAc

Sources & evidence

ORD record
ord-fa43245339f34a73975084265eff21d7
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

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