Hydroxyamine hydrochloride → 1-[2-amino-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

HRID 600395Notes

Reaction equation

HRID 600395 reaction equation
C(=[N:14][C:15]1[N:16]=[C:17]2[C:23]([C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:22][N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:18]2=[N:19][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO>CO>[NH2:14][C:15]1[N:16]=[C:17]2[C:23]([C:24](=[O:29])[C:25]([CH3:26])([CH3:27])[CH3:28])=[CH:22][N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:37])[CH3:36])[C:18]2=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 57831043HCID 57831043, compound

Product 1

HCID 578310481-[2-amino-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-oneYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[2-(benzhydrylidene-amino)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.670 g, 1.31 mmol), sodium acetate (0.258 g, 3.14 mmol) and hydroxylamine hydrochloride (0.164 g, 2.36 mmol) in 13 mL of methanol was stirred for 1 h, then concentrated to a residue. Column chromatography (10→50% EtOAc/hexanes) afforded 0.359 g (79%) of 1-[2-amino-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a white solid.

Workup

  1. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-174d5cbb59154644b7148a87b95a6e0d
Source dataset
uspto-grants-2011_03
Patent number
US07902197B2

Reaction notes

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