Phosphorus pentachloride → 1H-Pyrazolo[4,3-d]pyrimidine, 7-chloro-1,3-dimethyl-5-(1-methylethyl)-

HRID 2417671Notes

Reaction equation

HRID 2417671 reaction equation
[CH3:1][N:2]1[C:10]2[C:9](O)=[N:8][C:7]([CH:12]([CH3:14])[CH3:13])=[N:6][C:5]=2[C:4]([CH3:15])=[N:3]1.P(Cl)(Cl)(Cl)(Cl)[Cl:17]>P(Cl)(Cl)(Cl)=O>[Cl:17][C:9]1[C:10]2[N:2]([CH3:1])[N:3]=[C:4]([CH3:15])[C:5]=2[N:6]=[C:7]([CH:12]([CH3:14])[CH3:13])[N:8]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178433984HCID 178433984, compound

Product 1

HCID 140065561H-Pyrazolo[4,3-d]pyrimidine, 7-chloro-1,3-dimethyl-5-(1-methylethyl)-Yield 97.4%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 10 g (0.048 mol) of 1,3-dimethyl-5-isopropyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol and 10.2 g (0.049 mol) of phosphorus pentachloride in 70 ml of phosphorus oxychloride is stirred under reflux five hours and evaporated in vacuo. The residue is dissolved in 150 ml of methylene dichloride and stirred with 100 ml of a saturated solution of sodium bicarbonate. The organic layer is separated, dried over MgSO4, and evaporated in vacuo to to give 10.5 g of 7-chloro-1,3-dimethyl-5-isopropyl-1H-pyrazolo[4,3-d]pyrimidine, mp 87°-89° C. from pet ether.

Workup

  1. temperatureunder reflux five hours
  2. customevaporated in vacuo
  3. dissolutionThe residue is dissolved in 150 ml of methylene dichloride
  4. stirringstirred with 100 ml of a saturated solution of sodium bicarbonate
  5. customThe organic layer is separated
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-93e5149f6ab841788b93b07fb3b08038
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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