8-Chloro-3-ethyl-[1,2,4]triazolo[4,3-A]pyrazine → 3-Ethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

HRID 2091728Notes

Reaction equation

HRID 2091728 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH2:11][CH3:12])=[N:9][N:10]=2)[CH:5]=[CH:6][N:7]=1>CO.[Pt]=O>[ClH:1].[CH2:11]([C:8]1[N:4]2[CH2:5][CH2:6][NH:7][CH2:2][C:3]2=[N:10][N:9]=1)[CH3:12]

Participants

4

Reactant 1

HCID 299234618-Chloro-3-ethyl-[1,2,4]triazolo[4,3-A]pyrazine

Product 1

HCID 670584843-Ethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared from 8-chloro-3-ethyl-1,2,4-triazolo[4,3-a]pyrazine (2.70 g, 14.8 mmol, from Step A) and platinum oxide (0.4 g) in 200 mL of methanol in a paar shaker under hydrogen (50 psi) for 14 hours. Filtration through Celite followed by concentration gave the title compound as a solid. 1H NMR (500 MHz, CD3OD) δ 1.36 (t, 3H, J=6.0 Hz), 2.84 (q, 2H, J=6.0 Hz), 3.70 (t, 2H, J=8.0 Hz), 4.28 (t, 2H, J=8.0 Hz). 4.06(s, 2H). ESI-MS 153 (M+1).

Workup

  1. filtrationFiltration through Celite
  2. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-946ee0563a4f478e8e3609599dc3e5f7
Source dataset
uspto-grants-2013_05
Patent number
US08440668B2

Reaction notes

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