Phosphorus pentachloride → 7-Chloro-5-cyclopropyl-1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidine

HRID 2417669Notes

Reaction equation

HRID 2417669 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6](O)[C:7]3[N:12]([CH3:13])[N:11]=[C:10]([CH3:14])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)(Cl)[Cl:17]>P(Cl)(Cl)(Cl)=O>[Cl:17][C:6]1[C:7]2[N:12]([CH3:13])[N:11]=[C:10]([CH3:14])[C:8]=2[N:9]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[N:5]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178433983HCID 178433983, compound

Product 1

HCID 133384087-Chloro-5-cyclopropyl-1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidineYield 89.2%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 5-cyclopropyl-1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol (14.3 g, 0.07 mol) and 18 g (0.088 mol) phosphorus pentachloride in 150 ml of phosphorus oxychloride is stirred under reflux for seven hours and evaporated in vacuo. The residue is dissolved in methylene dichloride and stirred with a saturated aqueous solution of NaHCO3. The organic layer is separated, dried (MgSO4), and evaporated in vacuo to give 13.9 g (84%) of 7-chloro-5-cyclopropyl-1,3-dimethyl-pyrazolo[4,3-d]pyrimidine, mp 87°-90° C. from heptane.

Workup

  1. temperatureunder reflux for seven hours
  2. customevaporated in vacuo
  3. dissolutionThe residue is dissolved in methylene dichloride
  4. stirringstirred with a saturated aqueous solution of NaHCO3
  5. customThe organic layer is separated
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-7d3910dc38d3422dbdb7eecbb043a7be
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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