Methyl iodide → HCID 49869421, compound

HRID 570949Notes

Reaction equation

HRID 570949 reaction equation
[H-].[Na+].Cl.[C:4]1([C:10]2[N:11]=[C:12]([C:15]3[N:16]=[CH:17][N:18]4[C:23](=[O:24])[N:22]([CH2:25]C#C)[N:21]=[N:20][C:19]=34)[NH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].[CH3:30]I>CN(C=O)C>[CH3:25][N:22]1[C:23](=[O:24])[N:18]2[CH:17]=[N:16][C:15]([C:12]3[N:13]([CH3:30])[CH:14]=[C:10]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:11]=3)=[C:19]2[N:20]=[N:21]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compoundHCID 178456699HCID 178456699, compound

Product 1

HCID 49869421HCID 49869421, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 19 mg, 0.467 mmol) was added in portions to a solution of 8-(4-phenyl-1H-imidazol-2-yl)-3-(prop-2-ynyl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one hydrochloride (70 mg) in DMF (3 mL) and the mixture was sonicated several times until hydrogen evolution ceased. Methyl iodide (66 μL, 1.065 mmol) was added and the mixture was stirred overnight. The resulting solution was poured into ice and was then left at 4° C. for 5 hours. The precipitate was filtered and washed successively with water and diethyl ether. 10 mg of crude product obtained from a previous experiment was combined, and the crude mixture was absorbed on silica. The crude product was purified by flash chromatography using DCM:MeOH (95:5) as eluent to give the title compound as a bright yellow solid (25 mg, 23%). The NMR spectrum of the product showed that it contained ˜5/6% of either starting material or the regioisomer of the product. δH (DMSO-d6): 8.92 (1H, s), 7.89 (1H, s), 7.89-7.92 (2H, m), 7.38-7.42 (2H, m), 7.22-7.26 (1H, m), 3.98 (3H, s), 3.87 (3H, s).

Workup

  1. additionThe resulting solution was poured into ice
  2. waitwas then left at 4° C. for 5 hours
  3. filtrationThe precipitate was filtered
  4. washwashed successively with water and diethyl ether
  5. custom10 mg of crude product obtained from a previous experiment
  6. customthe crude mixture was absorbed on silica
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-2e4ad405e8be4b839549164d52d84ac4
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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