Phosphorus oxychloride → HCID 54181037, compound

HRID 54244Notes

Reaction equation

HRID 54244 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[C:5]([CH2:9][CH:10]=[C:11]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[Cl:20])[CH3:12])=[C:4]([CH3:21])[N:3]=1.P(Cl)(Cl)([Cl:24])=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[NH2:1][C:2]1[N:7]=[C:6]([Cl:24])[C:5]([CH2:9][CH:10]=[C:11]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[Cl:20])[CH3:12])=[C:4]([CH3:21])[N:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178441162HCID 178441162, compound

Product 1

HCID 54181037HCID 54181037, compoundYield 97.3%

Procedure

Under a nitrogen atmosphere, a stirred solution of 2.0 grams (0.006 mole) of 2-amino-4-hydroxy-6-methyl-5-[3-(2,5-dichlorophenyl)-2-butenyl]pyrimidine, 16.5 grams (0.107 mole) of phosphorus oxychloride, and 1.5 grams (0.007 mole) of phosphorus pentachloride is heated at reflux for about 18 hours. After this time the reaction mixture is slowly pipetted into wet ice during a 20 minute period. The mixture is then stirred until the ice melted, and the resultant solid is collected by filtration. The solid is dissolved in methylene chloride, and the solution is dried with magnesium sulfate. The mixture is filtered and the filtrate is concentrated under reduced pressure, yielding 2.0 grams of 2-amino-4-chloro-6-methyl-5-[3-(2,5-dichlorophenyl)-2-butenyl]pyrimidine; mp 97°-100° C. The NMR spectrum is consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 18 hours
  2. filtrationthe resultant solid is collected by filtration
  3. dissolutionThe solid is dissolved in methylene chloride
  4. dry with materialthe solution is dried with magnesium sulfate
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb0352d894e94278b20ddef69a480226
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Reaction notes

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