Dimethylformamide → HCID 68651257, compound

HRID 646747Notes

Reaction equation

HRID 646747 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.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>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][CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:9]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 10332062HCID 10332062, compound

Product 1

HCID 68651257HCID 68651257, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

3-Amino-6-(3-hydroxyphenyl)-N-methylpyrazine-2-carboxamide (179 mg, 0.8 mmol) was taken into DMF (3 mL) followed by addition of cesium carbonate (1.3 g, 4 mmol) and 2-(bromoethyl)benzene (550 uL, 4 mmol). The mixture was heated to 85° C. for 12 hours then allowed to cool to room temperature. 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 in vacuo followed by purification of the residue using silica gel flash chromatography using ethyl acetate:hexanes (2:3) as eluent. The pure fractions were combined and concentrated then dried in vacuo to give 3-amino-N-methyl-6-{3-[(2-phenylethyl)oxy]phenyl}pyrazine-2-carboxamide (86 mg, 31% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO): 8.83 (s, 1H), 8.82 (br m, 1H), 7.74 (d, 1H), 7.67 (tr, 1H), 7.38-7.31 (m, 6H), 7.26-7.22 (m, 1H), 6.95 (d tr, 1H), 4.31 (tr, 2H), 3.08 (tr, 2H), 2.85 (d, 3H); MS (EI) for C20H21N4O2: 349 (MH+).

Workup

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

Sources & evidence

ORD record
ord-5e8ca53281f0407a84b2e288ce520973
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

Loading…