Dimethylformamide → HCID 68651810, compound

HRID 646748Notes

Reaction equation

HRID 646748 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH:17][CH3:18])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=2)=[CH:6][N:7]=1.CN(C=O)C.[Br:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:15]([NH:17][CH3:18])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:26][CH2:25][Br:24])[CH:9]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78391,2-Dibromoethane2×HCID 10796Cesium carbonate2×HCID 10332062HCID 10332062, compound

Product 1

HCID 68651810HCID 68651810, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

3-Amino-6-(3-hydroxyphenyl)-N-methylpyrazine-2-carboxamide (1.01 g, 4.1 mmol) was taken into DMF (10 mL) followed by addition of 1,2-dibromoethane (10 mL) and cesium carbonate (2.7 g, 8.2 mmol). The mixture was warmed to 85° C. over 5 days followed by addition of another aliquot of cesium carbonate and 1,2-dibromoethane and heating was continued an additional 4 hours. The mixture was diluted with an excess of ethyl acetate and washed with water (3×) then brine and dried over anhydrous magnesium sulfate. Filtration and concentration ill vacuo followed by purification of the residue using silica gel flash chromatography using ethyl acetate:hexanes (1:1) as eluent. The pure fractions were combined and concentrated then dried in vacuo to give 3-amino-6-{3-[(2-bromoethyl)oxy]phenyl)-N-methylpyrazine-2-carboxamide (486 mg, 34% yield) was a yellow solid: MS (EI) for C14H16N4O2Br: 351, 353 (MH+).

Workup

  1. temperatureheating
  2. washwashed with water (3×)
  3. dry with materialbrine and dried over anhydrous magnesium sulfate
  4. filtrationFiltration and concentration ill vacuo
  5. customfollowed by purification of the residue
  6. concentrationconcentrated
  7. customthen dried in vacuo

Sources & evidence

ORD record
ord-dfb871afcf8a49a1b034511104eb334d
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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