(5-Nitro-pyrazin-2-yl)-(2-triethylsilanyloxy-ethyl)-amine → N-(2-triethylsilanyloxy-ethyl)-pyrazine-2,5-diamine

HRID 719993Notes

Reaction equation

HRID 719993 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10][CH2:11][CH2:12][O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])=[N:8][CH:9]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[CH2:19]([Si:14]([CH2:15][CH3:16])([CH2:17][CH3:18])[O:13][CH2:12][CH2:11][NH:10][C:7]1[CH:6]=[N:5][C:4]([NH2:1])=[CH:9][N:8]=1)[CH3:20]

Participants

4

Reactant 1

HCID 21897295(5-Nitro-pyrazin-2-yl)-(2-triethylsilanyloxy-ethyl)-amine

Product 1

HCID 21897274N-(2-triethylsilanyloxy-ethyl)-pyrazine-2,5-diamineYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (5-nitro-pyrazin-2-yl)-(2-triethylsilanyloxy-ethyl)-amine (530 mg, 1.78 mmol) in ethyl acetate (25 mL) was treated with 10% palladium on activated carbon (60 mg). The reaction mixture was then placed on a Parr shaker under a hydrogen atomsphere of 50 psi for 4 h. The catalyst was then filtered off through a pad of celite, and the celite pad was then washed well with ethyl acetate. The filtrate was then concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, ethyl acetate) afforded N-(2-triethylsilanyloxy-ethyl)-pyrazine-2,5-diamine (459 mg, 96%) as an orange-brown solid: (ES)+-HRMS m/e calcd for C12H24N4O2Si (M+H)+ 269.1792, found 269.1794.

Workup

  1. filtrationThe catalyst was then filtered off through a pad of celite
  2. washthe celite pad was then washed well with ethyl acetate
  3. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-1000e85066ed431bbbdd0f41bd1d7f5d
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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