Hydrochloric Acid → HCID 66733850, compound

HRID 1913229Notes

Reaction equation

HRID 1913229 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[C:15]([NH2:17])[N:14]4[N:18]=[CH:19][CH:20]=[C:13]4[N:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.CCO.O.Cl>C(Cl)Cl.O1CCOCC1>[NH2:17][C:15]1[N:14]2[N:18]=[CH:19][CH:20]=[C:13]2[N:12]=[C:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 667334895-(1,4-Dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 66733850HCID 66733850, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

In a 40 mL scintillation vial was combined 5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-7-amine (Int-5g, 5.54 mmol, 1.52 g), EtOH (10 mL), H2O (4 mL) and 4N HCl:dioxane (4 mL). The vial was capped, sealed and the reaction was heated to 80° C. overnight. After 18 hours, the reaction was cooled to room temperature and diluted with DCM (100 mL). The solution was washed with saturated NaHCO3(aq) and extracted with DCM twice more. The combined organics were dried over Na2SO4 and the solvent was removed in vacuo to yield 4-(7-aminopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone (Int-5h) (1.18 g, 93% yield) as a pale orange solid.

Workup

  1. customThe vial was capped
  2. customsealed
  3. temperaturethe reaction was cooled to room temperature
  4. washThe solution was washed with saturated NaHCO3(aq)
  5. extractionextracted with DCM twice more
  6. dry with materialThe combined organics were dried over Na2SO4
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-920a11ede20f46499615c82af0b3ed8f
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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