Methyl iodide → HCID 86640248, compound

HRID 222101Notes

Reaction equation

HRID 222101 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:8]3[C:12]([CH2:13][CH2:14][C:15]=2[CH:16]=1)=[N:11][N:10]([C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]=3)=[O:4].[H-].[Na+].[CH3:38]I>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:38])[C:7]2[C:8]3[C:12]([CH2:13][CH2:14][C:15]=2[CH:16]=1)=[N:11][N:10]([C:17]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH:9]=3)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86640249HCID 86640249, compound

Product 1

HCID 86640248HCID 86640248, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-trityl-1,4,5,7-tetrahydro-1,6,7-triaza-as-indacene-2-carboxylic acid methyl ester XVII (1.1 mmol) in dry DMF (5 mL), NaH (2 eq) was added, the mixture was stirred at rt for 15 min then methyl iodide (2 eq) was added and the mixture was stirred at rt for 2 h. The mixture was poured into aq saturated NaH2PO4, extracted with AcOEt and the organic layer washed with water, dried (Na2SO4) and concentrated. The crude material was triturated with ethanol and filtered. Obtained the title compound (76% yield). ESI (+) MS: m/z 474 (MH+). 1H NMR (300 MHz): 2.48-2.59 (m, 1H), 2.62-2.92 (m, 3H), 3.79 (s, 3H), 3.89 (s, 3H), 6.44 (s, 1H), 7.11-7.31 (m, 15H), 7.61 (s, 1H).

Workup

  1. stirringthe mixture was stirred at rt for 2 h
  2. extractionextracted with AcOEt
  3. washthe organic layer washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude material was triturated with ethanol
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e57856a331b04b71898c2947fccf1b50
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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