Methyl iodide → HCID 49869003, compound

HRID 570950Notes

Reaction equation

HRID 570950 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14]3[NH:15][C:16]([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)=[CH:17][N:18]=3)=[C:7]2[N:6]=[N:5]1)[C:2]#[CH:3].[H-].[Na+].[CH3:26]I>CN(C=O)C>[CH3:26][N:18]1[CH:17]=[C:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[N:15]=[C:14]1[C:13]1[N:12]=[CH:11][N:8]2[C:9](=[O:10])[N:4]([CH2:1][C:2]#[CH:3])[N:5]=[N:6][C:7]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136340691HCID 136340691, compound

Product 1

HCID 49869003HCID 49869003, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(Prop-2-ynyl)-8-(5-(thiophen-2-yl)-1H-imidazol-2-yl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one (0.15 mmol) was dissolved in dry DMF (1 mL) and cooled in ice under a nitrogen atmosphere. A 60% suspension of sodium hydride in mineral oil (0.17 mmol) was added in one portion and the reaction stirred on ice for 10 minutes. Methyl iodide (0.30 mmol) was then added dropwise to the reaction and the mixture stirred at room temperature for 24 hours. Solvent was then removed under vacuum and product isolated by preparative thin layer chromatography eluting with 2.5% MeOH/DCM. Yield 90%. δH (DMSO-d6) 8.97 (1H, s), 7.78 (1H, s), 7.40 (1H, dd, J=5.2, 1.2), 7.33 (1H, dd, J=3.6, 1.2), 7.08 (1H, m), 5.13 (2H, d, J=2.4), 3.96 (3H, s), 3.52 (1H, t, J=2.4).

Workup

  1. temperaturecooled in ice under a nitrogen atmosphere
  2. stirringthe mixture stirred at room temperature for 24 hours
  3. customSolvent was then removed under vacuum and product
  4. customisolated by preparative thin layer chromatography
  5. washeluting with 2.5% MeOH/DCM

Sources & evidence

ORD record
ord-d2f4895496284a8399f571c9234ec858
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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