Phosphorus oxychloride → 7-Chloro-1-ethyl-1H-pyrazolo[4,3-d]pyrimidine

HRID 573345Notes

Reaction equation

HRID 573345 reaction equation
[CH2:1]([N:3]1[C:11]2[C:10](O)=[N:9][CH:8]=[N:7][C:6]=2[CH:5]=[N:4]1)[CH3:2].O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:10]1[C:11]2[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=2[N:7]=[CH:8][N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178463033HCID 178463033, compound

Product 1

HCID 714458087-Chloro-1-ethyl-1H-pyrazolo[4,3-d]pyrimidine

Conditions

Temperature
100 °C

Procedure

A mixture of 1-ethyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol (2.91 g) and POCl3 (30 mL) was stirred at 100° C. overnight. The mixture was concentrated under reduced pressure. The residue was neutralized with saturated NaHCO3 aqueous solution and extracted with AcOEt. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (2.14 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-dfa8156422914e4a99cd25b0ab75f904
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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