Hydrochloric Acid → 5-Chloro-1H-pyrazolo(4,3-d)pyrimidine

HRID 243336Notes

Reaction equation

HRID 243336 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[CH:5][C:6]2[N:11](C(=O)C)[N:10]=[CH:9][C:7]=2[N:8]=1>O1CCCC1>[Cl:2][C:3]1[N:4]=[CH:5][C:6]2[NH:11][N:10]=[CH:9][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59797350HCID 59797350, compound

Product 1

HCID 597969475-Chloro-1H-pyrazolo(4,3-d)pyrimidineYield 47.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrochloric acid (70 mL, 8%) was added dropwise to a solution of 1-[5-chloro-1H-pyrazolo[4,3-d]pyrimidin-1-yl]ethan-1-one (7 g, 33.83 mmol, 1.00 equiv, 95%) in tetrahydrofuran (70 mL) at 50° C. The resulting solution was refluxed for 30 min and then extracted with 2×100 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum to give 2.5 g (45%) of 5-chloro-1H-pyrazolo[4,3-d]pyrimidine as a white solid.

Workup

  1. temperatureThe resulting solution was refluxed for 30 min
  2. extractionextracted with 2×100 mL of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-64f3d0304fd8400d87ba03b2ba0b13f8
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…