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

HRID 2036915Notes

Reaction equation

HRID 2036915 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.[OH-].[NH4+:13]>>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:13])[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 88%

Conditions

Temperature
85 °C

Procedure

To the reaction flask, 5,7-dichloropyrazolo[1,5-a]pyrimidine (3 g, 16 mmol) was added along with ammonium hydroxide solution (48 mL). The heterogeneous reaction was refluxed at 85° C. for 12 hours. After cooling to room temperature, the mixture was filtered, washed with water, and dried under vacuum overnight. The product, 5-chloropyrazolo[1,5-a]pyrimidin-7-amine, was collected as an off-white solid in 88% yield. LCMS (M+1=169)

Workup

  1. customThe heterogeneous reaction
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered
  4. washwashed with water
  5. customdried under vacuum overnight
  6. customThe product, 5-chloropyrazolo[1,5-a]pyrimidin-7-amine, was collected as an off-white solid in 88% yield

Sources & evidence

ORD record
ord-1d8f764ff4c04f9bbef5a6a2f1a5ce1d
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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