Triethylamine → 5-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine

HRID 624690Notes

Reaction equation

HRID 624690 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.CCN(CC)CC.[CH:19]1([NH2:22])[CH2:21][CH2:20]1>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:22][CH:19]2[CH2:21][CH2:20]2)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidine

Product 1

HCID 581966065-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amineYield 70.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To 5,7-dichloropyrazolo[1,5-a]pyrimidine (200 mg, 1.06 mmol) in ACN was added Et3N (148 μl, 1.06 mmol) and cyclopropylamine (75 μl, 1.06 mmol). The reaction was refluxed at 80° C. overnight. The mixture was concentrated under reduced pressure, dissolved in DCM, and washed with water. The resulting organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 156 mg of 5-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine (70% yield). LCMS (M+1=209)

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in DCM
  3. washwashed with water
  4. dry with materialThe resulting organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d784bf12373e48f48cc28f5bfcc160ed
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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