Methyl iodide → HCID 24990699, compound

HRID 222137Notes

Reaction equation

HRID 222137 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([N:11]=1)=[C:9]1[NH:12][C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:14]([C:15]([NH2:17])=[O:16])[C:8]1=[CH:7][CH:6]=2.[C:24](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([N:11]=1)=[C:9]1[N:12]([CH3:24])[C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:14]([C:15]([NH2:17])=[O:16])[C:8]1=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 24990698HCID 24990698, compound

Product 1

HCID 24990699HCID 24990699, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 8-amino-2-phenyl-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid amide N9 (0.16 mmol) in dry DMF (5 mL), caesium carbonate (0.7 mmol) and methyl iodide (0.7 mmol) were added. The reaction mixture was heated at 70° C. in a sealed tube for 1 h then the solvent was evaporated. The solid residue was washed with water and dried, giving the title compound (78% yield). ESI (+) MS: m/z 391 (MH+). 1H NMR: 4.21 (s, 3H), 6.15 (bs, 1H), 6.76 (bs, 2H), 7.08 (bs, 1H), 7.42 (d, J=8.50, 1H), 7.52-7.65 (m, 5H), 7.83 (d, J=8.50, 1H), 9.03 (s, 1H).

Workup

  1. customthe solvent was evaporated
  2. washThe solid residue was washed with water
  3. customdried

Sources & evidence

ORD record
ord-ffec3e308e0e45d9a2414c63dc5293b6
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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