Nitrogen → 5-(tetrahydro-2H-pyran-4-yl)pyrazin-2-amine

HRID 595786Notes

Reaction equation

HRID 595786 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH2:3][CH2:2]1.N#N.[H][H]>CO.[Pd]>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[N:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 1180459175-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 457888255-(tetrahydro-2H-pyran-4-yl)pyrazin-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amine (2.7 g, 15.24 mmol) and Pd—C (10%, Degussa type) (1.6 g, 1.5 mmol) in MeOH (50 mL) was degassed by N2 stream for 15 min. After equipped with hydrogen gas balloon, the reaction mixture was stirred for 15 h at room temperature. The crude product was filtered off through celite pad and washed with EtOAc. The volatile material was concentrated in vacuo yielding 5-(tetrahydro-2H-pyran-4-yl)pyrazin-2-amine and was used for the next step. LCMS (m/z): 180.3 (MH+), 0.28 min.

Workup

  1. filtrationThe crude product was filtered off through celite pad
  2. washwashed with EtOAc
  3. concentrationThe volatile material was concentrated in vacuo

Sources & evidence

ORD record
ord-aa8dce128a934002927b0f8dc432ea4f
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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