Dimethylformamide → 5-Chloropyrazolo(1,5-a)pyrimidine-3-carbaldehyde

HRID 383685Notes

Reaction equation

HRID 383685 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][CH:10]=[C:4]2[N:3]=1.O=P(Cl)(Cl)Cl.[OH-].[Na+].CN([CH:21]=[O:22])C>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([CH:21]=[O:22])=[C:4]2[N:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 210717595-Chloropyrazolo(1,5-a)pyrimidine

Product 1

HCID 581964015-Chloropyrazolo(1,5-a)pyrimidine-3-carbaldehydeYield 70%

Procedure

To 5-chloropyrazolo[1,5-a]pyrimidine (200 mg, 1.31 mmol) in 1.5 mL DMF was added POCl3 (358 μL, 3.92 mmol). The reaction was stirred at room temperature overnight. The mixture was cooled to 0° C. in ice bath and then neutralized with 6M NaOH. The solid formed was isolated by filtration and air dried to give 165 mg of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde as yellow solid (70% yield). LCMS (M+1=182)

Workup

  1. temperatureThe mixture was cooled to 0° C. in ice bath
  2. customThe solid formed
  3. customwas isolated by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-7c2aa42451754665a55ffd33f1cfb810
Source dataset
uspto-grants-2013_02
Patent number
US08367681B2

Reaction notes

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