Methyl iodide → HCID 49869139, compound

HRID 570959Notes

Reaction equation

HRID 570959 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[CH:12][N:13]2[C:18](=[O:19])[N:17]([CH3:20])[N:16]=[N:15][C:14]=12.[H-].[Na+].[CH3:23]I>CN(C=O)C>[CH3:20][N:17]1[C:18](=[O:19])[N:13]2[CH:12]=[N:11][C:10]([C:2]3[N:1]([CH3:23])[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[C:14]2[N:15]=[N:16]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135985849HCID 135985849, compound

Product 1

HCID 49869139HCID 49869139, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of 8-(1H-benzo[d]imidazol-2-yl)-3-methylimidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one (0.54 mmol, 0.144 grams, 1 eq.) in anhydrous DMF (2.5 mL) was added sodium hydride 60% in mineral oil (0.59 mmol, 24 mg, 1.1 eq.) portion-wise. The formed suspension was stirred at low temperature for 10 minutes and methyl iodide (1.07 mmol, 67 μL, 2 eq.) was added into it in one portion. The suspension was stirred over night at room temperature. The reaction mixture was filtered and the obtained solid was washed with water, acetonitrile and ethyl acetate, and dried under vacuum to give the title compound. Yield: 55%. δH (DMSO-d6) 9.02 (1H, s), 7.77 (1H, d, J: 8.09), 7.68 (1H, d, J: 8.12), 7.36 (1H, m), 7.32 (1H, m), 4.14 (3H, s), 3.90 (3H, s).

Workup

  1. stirringThe suspension was stirred over night at room temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe obtained solid was washed with water, acetonitrile and ethyl acetate
  4. customdried under vacuum

Sources & evidence

ORD record
ord-7f57a4aeee354360a25cbb7dc8c23e67
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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