Hydroxyamine hydrochloride → 6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine

HRID 905989Notes

Reaction equation

HRID 905989 reaction equation
C(=[N:14][C:15]1[N:16]=[C:17]2[CH:23]=[C:22]([CH3:24])[N:21]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]2=[N:19][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])=O.[Na+].NO.Cl>CO>[CH3:24][C:22]1[N:21]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[C:18]2=[N:19][CH:20]=[C:15]([NH2:14])[N:16]=[C:17]2[CH:23]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86642306benzhydrylidene-[6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-amine

Product 1

HCID 673853776-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamineYield 58.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzhydrylidene-[6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-amine (0.158 g, 0.357 mmol), NaOAc (70 mg, 0.857 mmol) and NH2OH HCl (45 mg, 0.643 mmol) were dissolved in MeOH (4 mL) and stirred at RT overnight, and partitioned between EtOAc and brine. The organic layer was dried (MgSO4), filtered, concentrated, and purified by SiO2 chromatography (24 g SiO2, hexanes/EtOAc 0-90% EtOAc) to give 58 mg of 6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine as a yellow solid (58% yield).

Workup

  1. custompartitioned between EtOAc and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by SiO2 chromatography (24 g SiO2, hexanes/EtOAc 0-90% EtOAc)

Sources & evidence

ORD record
ord-fc8c839f376b412fa1442760272f3532
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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