Water → HCID 70867226, compound

HRID 1878560Notes

Reaction equation

HRID 1878560 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1.O.[NH2:24][NH2:25].O>O1CCOCC1>[N:8]1([C:6]2[N:5]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:16]=[C:4]3[N:3]=[C:2]([NH:24][NH2:25])[CH:7]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 585311415-Chloro-7-(4-morpholinyl)-2-phenylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 70867226HCID 70867226, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-chloro-7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidine (150 mg, 0.48 mM) in 1,4-dioxane (5.0 mL), there was added hydrazine monohydrate (0.23 mL, 4.8 mM) and the mixture was stirred at 90° C. for 14 hours. The reaction mixture was cooled down to room temperature, then water was added thereto and the mixture was extracted with ethyl acetate. The organic phase thus obtained was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to thus give the title compound (133 mg, yield: 90%). MS (ESI) m/z (M+H)+ 311

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic phase thus obtained
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c022a5c52e8486b802449d6d1dd9424
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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