Phosphorus oxychloride → 2-Amino-4-chloro-6-phenylpyrimidine

HRID 2291345Notes

Reaction equation

HRID 2291345 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:13][C:12]([NH2:14])=[N:11][C:9](=O)[CH:8]=2)=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:9]1[CH:8]=[C:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[N:13]=[C:12]([NH2:14])[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178508963HCID 178508963, compound

Product 1

HCID 2408022-Amino-4-chloro-6-phenylpyrimidine

Procedure

To 10.0 g (53 mM) of 6-phenylisocytosine is added 80 ml of phosphorus oxychloride. The mixture is heated to reflux, and refluxed until solution is complete (about 30 minutes). The solution is then cooled and evaporated to dryness under vacuum at 45° C. The resulting oil is poured into 300 ml of ice water, with vigorous stirring, and the remaining oil washed into the aqueous mixture with additional 100 ml of water. The entire aqueous mixture is neutralized to pH 8 with concentrated ammonium hydroxide, filtered, and solids washed well with water until water wash is neutral. Dry at 60° in a vacuum oven to yield 9.2 g of 4-chloro-6-phenyl-2-pyrimidinamine.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperaturerefluxed until solution
  4. custom(about 30 minutes)
  5. temperatureThe solution is then cooled
  6. customevaporated to dryness under vacuum at 45° C
  7. additionThe resulting oil is poured into 300 ml of ice water, with vigorous stirring
  8. washthe remaining oil washed into the aqueous mixture with additional 100 ml of water
  9. filtrationfiltered
  10. washsolids washed well with water until water
  11. washwash
  12. customDry at 60° in a vacuum oven

Sources & evidence

ORD record
ord-04bcccbc77e04a2189a5f50e6321ca04
Source dataset
uspto-grants-1989_01
Patent number
US04795812

Reaction notes

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