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

HRID 624691Notes

Reaction equation

HRID 624691 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 excess POCl3 then the mixture was neutralized with 1M NaOH. DCM 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 excess POCl3
  3. additionDCM 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-7105e654123441e9aef2589b08cb054b
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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