3-cyclopropyl-1H-pyrazol-5-amine → HCID 178516372, compound

HRID 1951283Notes

Reaction equation

HRID 1951283 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH2:9])[CH:5]=2)[CH2:3][CH2:2]1.C([O:12][C:13](=O)/[CH:14]=[CH:15]\[O-])C.[Na+]>CCO.C1(C)C=CC=CC=1>[CH:1]1([C:4]2[CH:5]=[C:6]3[N:9]=[CH:15][CH:14]=[C:13]([OH:12])[N:7]3[N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 58190618sodium (Z)-3-ethoxy-3-oxoprop-1-en-1-olate

Product 1

HCID 178516372HCID 178516372, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-cyclopropyl-1H-pyrazol-3-amine (415 mg, 3.37 mmol) and sodium (Z)-3-ethoxy-3-oxoprop-1-en-1-olate (0.791 g, 5.73 mmol) in EtOH (3 mL) and toluene (1 mL) was heated to 80° C. in a resealable tube. After 16 hrs the solvent was removed in vacuo. The resulting residue was dissolved in a minimal amount of warm water and triturated with 1 N HCl with cooling (0° C.) until the pH ˜1. The resulting solid was filtered and washed with water to afford 2-cyclopropylpyrazolo[1,5-a]pyrimidin-7-ol as an off-white solid that was advanced without further purification. M+H+ found=176.2.

Workup

  1. customAfter 16 hrs the solvent was removed in vacuo
  2. dissolutionThe resulting residue was dissolved in a minimal amount of warm water
  3. customtriturated with 1 N HCl
  4. temperaturewith cooling (0° C.) until the pH ˜1
  5. filtrationThe resulting solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-546e3628c4804bafaa37b52b4cf1ea13
Source dataset
uspto-grants-2013_03
Patent number
US08404694B2

Reaction notes

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