Hydrazine hydrate (1:1) → HCID 70999553, compound

HRID 1878580Notes

Reaction equation

HRID 1878580 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:18]=[N:19][CH:20]=[N:21][CH:22]=3)[CH:16]=[C:4]2[N:3]=1.O.[NH2:24][NH2:25]>O1CCOCC1>[N:8]1([C:6]2[N:5]3[N:14]=[C:15]([C:17]4[CH:18]=[N:19][CH:20]=[N:21][CH:22]=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

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86659730HCID 86659730, compound

Product 1

HCID 70999553HCID 70999553, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

There was suspended, in 1,4-dioxane (1.0 mL), 5-chloro-7-morpholin-4-yl-2-pyrimidin-5-yl-pyrazolo[1,5-a]pyrimidine (20 mg, 2.4 mM) prepared in the preceding step 1, then hydrazine monohydrate (29 μL, 0.6 mM) was added to the suspension and the mixture was stirred for 6 hours while refluxing the same with heating. After the stirring operation, the reaction liquid was concentrated, the concentrate was diluted with water and then the mixture was extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate and the solvent was distilled off to thus give a crude product of the title compound (18 mg, yield: 96%).

Workup

  1. temperaturewhile refluxing the same
  2. temperaturewith heating
  3. customAfter the stirring operation, the reaction liquid
  4. concentrationwas concentrated
  5. additionthe concentrate was diluted with water
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-70e6597b77ac42d6ab469f475195212f
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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