Benzyl Alcohol → HCID 68650821, compound

HRID 646751Notes

Reaction equation

HRID 646751 reaction equation
[NH2:1][C:2]1[CH:3]([C:17]([O:19][CH3:20])=[O:18])[N:4](C)[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]Cl)[CH:9]=2)=[CH:6][N:7]=1.[CH2:21]([OH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[Ag]=O>[NH2:1][C:2]1[C:3]([C:17]([O:19][CH3:20])=[O:18])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:28][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:9]=2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 68650701HCID 68650701, compound

Product 1

HCID 68650821HCID 68650821, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Conditions

Temperature
110 °C

Procedure

Methyl 3-amino-6-(3-chloromethylphenyl)-N-methylpyrazine-2-carboxylate (18 mg, 0.06 mmol) and silver oxide (15 mg, 0.06 mmol) were added to benzyl alcohol (2 mL) and the mixture was heated to 110° C. over 15 hours. The benzyl alcohol was removed in vacuo and the residue purified by silica gel flash chromatography using ethyl acetate:hexanes (1:1) as eluent. The pure fractions were combined and concentrated then dried ill vacuo to give methyl 3-amino-6-(3-{[(phenylmethyl)oxy]methyl}phenyl)pyrazine-2-carboxylate (5.8 mg, 28% yield) as a yellow solid: MS (EI) for C20H20N3O3: 350 (MH+).

Workup

  1. customThe benzyl alcohol was removed in vacuo
  2. customthe residue purified by silica gel flash chromatography
  3. concentrationconcentrated
  4. customthen dried ill vacuo

Sources & evidence

ORD record
ord-85c8658612004a018c09fed6803ebc62
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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