Methyl iodide → HCID 22724429, compound

HRID 2086889Notes

Reaction equation

HRID 2086889 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:12](=[O:13])[C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[N:10][C:9]3[CH:19]=[CH:20][CH:21]=[N:22][C:8]2=3)[CH:2]=1.IC.[C:31](=O)([O-])[O-].[K+].[K+].[Na]>CN(C)C=O.C(OCC)(=O)C>[C:1]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:12](=[O:13])[C:11]([CH2:14][CH2:15][C:16]([O:18][CH3:31])=[O:17])=[N:10][C:9]3[CH:19]=[CH:20][CH:21]=[N:22][C:8]2=3)[CH:2]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5360545SodiumHCID 22724201HCID 22724201, compound

Product 1

HCID 22724429HCID 22724429, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(3-biphenylyl)-2-(2-carboxyethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (80 mg), iodomethane (0.04 ml) and potassium carbonate (90 mg) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 1 hour. Then the mixture was poured into a mixture of ethyl acetate and aqueous sodium bicarbonte. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was crystallized from methanol to give 4-(3-biphenylyl)-2-(2-methoxycarbonylethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (71 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-2e2667eed9e3447a81f3f2c20740c628
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

Loading…