1,4-Dioxane hydrochloride → HCID 86686229, compound

HRID 1021270Notes

Reaction equation

HRID 1021270 reaction equation
[CH3:1][O:2][CH:3]1[CH2:6][N:5]([C:7]2[N:12]=[CH:11][C:10]([C:13]3[CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH:18]=3)=[CH:9][N:8]=2)[CH2:4]1.Cl.O1CCOCC1>[C].[Pd].CCO>[CH3:1][O:2][CH:3]1[CH2:4][N:5]([C:7]2[N:8]=[CH:9][C:10]([CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)=[CH:11][N:12]=2)[CH2:6]1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68308903HCID 68308903, compound

Product 1

HCID 86686229HCID 86686229, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×

Procedure

tert-Butyl 4-[2-(3-methoxyazetidin-1-yl)pyrimidin-5-yl]-3,6-dihydropyridine-1(2H)-carboxylate (483 mg) was mixed with EtOH (5 ml), and 10% palladium carbon (100 mg) was added thereto, followed by stirring at room temperature for 5 hours under hydrogen atmosphere. The reaction mixture was filtered using Celite as a filtration adjuvant, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/EtOAc). The purified product thus obtained was mixed with EtOH (5 ml), and 4 M hydrogen chloride/dioxane (3.5 ml) was added thereto, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and then mixed with EtOH (5 ml), and potassium carbonate (2.0 g) was added thereto, followed by stirring at 80° C. for 2 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to obtain 2-(3-methoxyazetidin-1-yl)-5-(piperidin-4-yl)pyrimidine (143 mg).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)
  5. customThe purified product thus obtained
  6. additionwas added
  7. stirringby stirring at room temperature overnight
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. additionmixed with EtOH (5 ml), and potassium carbonate (2.0 g)
  10. additionwas added
  11. stirringby stirring at 80° C. for 2 hours
  12. filtrationThe reaction mixture was filtered
  13. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c85c1c3da2b4459191599a2d82d02837
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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