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

HRID 2036991Notes

Reaction equation

HRID 2036991 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 acetonitrile was added Et3N (148 μl, 1.06 mmol) and cyclopropylamine (75 μl, 1.06 mmol). The reaction was heated at 80° C. overnight. The mixture was concentrated under reduced pressure, dissolved in dichloromethane, 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 dichloromethane
  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-7cb31d3713c34329aabcfea75bd1457f
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

Loading…