Ammonium Hydroxide → 5-Chloropyrazolo[1,5-a]pyrimidin-7-amine

HRID 2368965Notes

Reaction equation

HRID 2368965 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[NH4+:12].[OH-]>>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:12])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidine

Product 1

HCID 231319095-Chloropyrazolo[1,5-a]pyrimidin-7-amineYield 100%

Conditions

Temperature
85 °C

Procedure

To 5,7-dichloropyrazolo[1,5-a]pyrimidine (7.6 g, 40.4 mmol) in a sealed vessel was added NH4OH (100 mL). The vessel was then sealed and heated at 85° C. for 2.5 hours, at which time the consistency of the white solid had changed (from foamy white solid to free-flowing white solid). The vessel was removed from the heat source and allowed to cool to room temperature overnight. On cooling, the contents of the vessel were collected and dried by vacuum filtration giving 5-chloropyrazolo[1,5-a]pyrimidin-7-amine as a yellow-tinged white solid (6.8 g, 40.3 mmol, 100%).

Workup

  1. customThe vessel was then sealed
  2. customThe vessel was removed from the heat source
  3. temperatureto cool to room temperature overnight
  4. temperatureOn cooling
  5. customthe contents of the vessel were collected
  6. customdried by vacuum filtration

Sources & evidence

ORD record
ord-0567c87852f64f40ac67b203fa261a41
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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