Phosphorus oxychloride → 7-CHLOROPYRAZOLO[1,5-A]PYRIMIDINE

HRID 525015Notes

Reaction equation

HRID 525015 reaction equation
[N:1]1[N:5]2[C:6](=O)[CH:7]=[CH:8][NH:9][C:4]2=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:13])=O.C(N(C(C)C)CC)(C)C>>[Cl:13][C:6]1[N:5]2[N:1]=[CH:2][CH:3]=[C:4]2[N:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178516532HCID 178516532, compound

Product 1

HCID 122816477-CHLOROPYRAZOLO[1,5-A]PYRIMIDINEYield 71%

Conditions

Temperature
90 °C

Procedure

Pyrazolo[1,5-a]pyrimidin-7(4H)-one (0.50 g, 3.70 mmols), phosphorus oxychloride (0.88 ml, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13 ml, 0.74 mmols) were mixed and stirred at 90° C. overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuum. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1) to afford the expected compound (83 mg, 71%).

Workup

  1. additionIt was poured onto water/ice
  2. extractionextracted with dichloromethane
  3. washwashed with brine
  4. customIt was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customIt was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1)

Sources & evidence

ORD record
ord-d07c9e370de242adad4af30969835e36
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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