Dimethylformamide → 3-((7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile

HRID 2036965Notes

Reaction equation

HRID 2036965 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][CH:13]=[C:9]3[N:8]=[C:7]([CH2:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[CH:6]=2)[CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.CN([CH:31]=[O:32])C>>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:31]=[O:32])=[C:9]3[N:8]=[C:7]([CH2:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[CH:6]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 672169163-((7-(Cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile

Product 1

HCID 583146163-((7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrileYield 37%

Procedure

To 3-((7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile (69 mg, 0.24 mmol) in DMF (0.6 mL), POCl3 (130 μL, 1.4 mmol) was added at room temperature. After the addition was complete, the reaction was stirred for 1 hour at room temperature. Then, the reaction was quenched by addition to ice cold 6N NaOH. The mixture was diluted with water and the solid was collected by filtration. The solid was washed several more times with water then dried under vacuum overnight. The product, 3-((7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 37% yield. LCMS (M+1=318)

Workup

  1. additionAfter the addition
  2. customThen, the reaction was quenched by addition to ice cold 6N NaOH
  3. additionThe mixture was diluted with water
  4. filtrationthe solid was collected by filtration
  5. washThe solid was washed several more times with water
  6. customthen dried under vacuum overnight
  7. customThe product, 3-((7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 37% yield

Sources & evidence

ORD record
ord-ec7904f84ae042659f8780f9759663a4
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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