Hydrazine hydrate (1:1) → HCID 70999566, compound

HRID 1878577Notes

Reaction equation

HRID 1878577 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][C:20]([CH3:23])=[CH:21][CH:22]=3)[CH:16]=[C:4]2[N:3]=1.O.[NH2:25][NH2:26]>O1CCOCC1>[CH3:23][C:20]1[N:19]=[CH:18][C:17]([C:15]2[CH:16]=[C:4]3[N:3]=[C:2]([NH:25][NH2:26])[CH:7]=[C:6]([N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)[N:5]3[N:14]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86659729HCID 86659729, compound

Product 1

HCID 70999566HCID 70999566, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

There was suspended, in 1,4-dioxane (24 mL), 5-chloro-2-(6-methyl-pyridin-3-yl)-7-morpholin-4-yl-pyrazolo[1,5-a]-pyrimidine (0.79 g, 2.4 mM) prepared in the preceding step 1, then hydrazine monohydrate (1.2 mL, 24 mM) was added to the suspension and the mixture was stirred for 15 hours, while refluxing the same with heating. After the stirring operation, the reaction liquid was concentrated, the concentrate was diluted with water and then extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate and then the solvent was distilled off to thus give a crude product of the title compound (210 mg, yield: 27%).

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. extractionextracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-d62ca06bc99a4f20afba16caeed65715
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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