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

HRID 624731Notes

Reaction equation

HRID 624731 reaction equation
[CH2:1]([S:8][C:9]1[N:14]2[N:15]=[CH:16][CH:17]=[C:13]2[N:12]=[C:11]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.CN([CH:34]=[O:35])C>>[CH2:1]([S:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([CH:34]=[O:35])=[C:13]2[N:12]=[C:11]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 583150077-(benzylthio)-N-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-amine

Product 1

HCID 583138967-(Benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehydeYield 83%

Procedure

To 7-(benzylthio)-N-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-amine (4.1 g, 11.3 mmol) in DMF (42 mL), POCl3 (6.3 mL, 67.6 mmol) was added dropwise at room temperature. After the addition was complete, the reaction was stirred for 3 hours at room temperature. Then, the reaction was quenched by slow 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, 7-(benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde, was collected as a solid in 83% yield. LCMS (M+1=395)

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. customthen dried under vacuum overnight
  7. customThe product, 7-(benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde, was collected as a solid in 83% yield

Sources & evidence

ORD record
ord-f50c4256c3264a8f97a948a9dfc3f329
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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