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

HRID 383699Notes

Reaction equation

HRID 383699 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.CN([CH:19]=[O:20])C>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([CH:19]=[O:20])=[C:4]2[N:3]=1

Participants

4

Reactant 3

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

Product 1

HCID 581964015-Chloropyrazolo(1,5-a)pyrimidine-3-carbaldehydeYield 82%

Procedure

To 5-chloropyrazolo[1,5-a]pyrimidine (5.0 g, 32.5 mmol) in DMF was added POCl3 (7.5 mL, 81.2 mmol). The mixture was stirred at room temperature overnight. Ice was added to quench POCl3, then the mixture was neutralized with 1M NaOH. The resulting yellow precipitate was filtered and dried to yield 4.85 g (82% yield) of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde as yellow solid. LCMS (M+1=182)

Workup

  1. additionIce was added
  2. customto quench POCl3
  3. filtrationThe resulting yellow precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-a6bf1d10032c4681b7f523157488e8b6
Source dataset
uspto-grants-2013_02
Patent number
US08367681B2

Reaction notes

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