Dimethylformamide → HCID 58314515, compound

HRID 624686Notes

Reaction equation

HRID 624686 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[N:5]2[N:16]=[CH:17][CH:18]=[C:4]2[N:3]=1.O=P(Cl)(Cl)Cl.CN([CH:27]=[O:28])C>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])[N:5]2[N:16]=[CH:17][C:18]([CH:27]=[O:28])=[C:4]2[N:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 58972302HCID 58972302, compound

Product 1

HCID 58314515HCID 58314515, compoundYield 27%

Procedure

To tert-butyl 5-chloropyrazolo[1,5-a]pyrimidin-7-ylcarbamate (3.7 g, 13.8 mmol) in DMF (36 mL), POCl3 (7.7 mL, 82.9 mmol) was added dropwise at 0° C. After the addition was complete, the reaction was allowed to warm to room temperature and stirred for 8 hours. Then, the reaction was quenched by slow addition to ice cold 6N NaOH. The mixture was diluted with water then the solid was collected by filtration. The solid was washed several more times with water and dried under vacuum overnight. The product, tert-butyl 5-chloro-3-formylpyrazolo[1,5-a]pyrimidin-7-ylcarbamate, was collected as a solid in 27% yield. The product did not ionize on LCMS unless first deprotected using TFA/DCM (1:1). LCMS (M+1=197)

Workup

  1. additionAfter the addition
  2. customThen, the reaction was quenched by slow 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. customdried under vacuum overnight
  7. customThe product, tert-butyl 5-chloro-3-formylpyrazolo[1,5-a]pyrimidin-7-ylcarbamate, was collected as a solid in 27% yield

Sources & evidence

ORD record
ord-877baac3a4824423a77f65f4cc77785e
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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