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

HRID 2036919Notes

Reaction equation

HRID 2036919 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-2e6684436d0947e696da9047e8715ba5
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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