Ethanol → HCID 66733850, compound

HRID 2047057Notes

Reaction equation

HRID 2047057 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.O1CCOCC1>C(Cl)Cl>[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

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 312751,4-DioxaneHCID 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 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

In a 40 mL scintillation vial is combined 5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-7-amine (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 mixture 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 are dried over Na2SO4 and the solvent removed in vacuo to yield 4-(7-aminopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone (1.18 g, 93% yield) as pale orange solid.

Workup

  1. customThe vial was capped
  2. customsealed
  3. temperaturethe reaction mixture 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 are dried over Na2SO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2f55afef3ace4c72b94aa03ca1522551
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

Loading…