5-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-2-amine → 5-(tetrahydro-2H-thiopyran-4-yl)pyridin-2-amine

HRID 595813Notes

Reaction equation

HRID 595813 reaction equation
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH2:3][CH2:2]1>CO.C(Cl)Cl.[Pd]>[S:1]1[CH2:2][CH2:3][CH:4]([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 1180456455-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-2-amine

Product 1

HCID 1180456525-(tetrahydro-2H-thiopyran-4-yl)pyridin-2-amineYield 91.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-2-amine (260 mg, 1.35 mmol), Pd/C (36 mg, 0.33 mmol) in methanol (16 mL) was stirred under hydrogen at ambient temperature for 16 h. The reaction mixture was diluted with DCM (80 mL), and was filtered through Celite. The filtrate was concentrated to give 5-(tetrahydro-2H-thiopyran-4-yl)pyridin-2-amine (240 mg, 91% yield) as yellow color solid. LCMS (m/z): 195 (MH+), 0.46 min.

Workup

  1. filtrationwas filtered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4a23599ccaad4baab79178c67865d0b2
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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