Dimethylformamide → 5-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 624774Notes

Reaction equation

HRID 624774 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1.O=P(Cl)(Cl)Cl.CN([CH:23]=[O:24])C>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:23]=[O:24])=[C:4]2[N:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 581966065-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 581966475-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Procedure

To 5-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine (156 mg, 0.75 mmol) in DMF was added POCl3 (205 μl, 2.25 mmol). The mixture was stirred at room temperature for 3 hours. Ice was added to quench POCl3, and then the mixture was neutralized with 1 M NaOH. Dichloromethane was added and the product was extracted three times. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde. Some residual DMF could not be removed. LCMS (M+1=237)

Workup

  1. additionIce was added
  2. customto quench POCl3
  3. additionDichloromethane was added
  4. extractionthe product was extracted three times
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50b21771e8424d96b006ab0b73091e74
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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