Methyl iodide → HCID 49869138, compound

HRID 570961Notes

Reaction equation

HRID 570961 reaction equation
[H-].[Na+].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[N:13]=[CH:14][N:15]2[C:20](=[O:21])[N:19]([CH2:22][C:23]#[CH:24])[N:18]=[N:17][C:16]=12.[CH3:25]I>CN(C=O)C>[CH3:25][N:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:3]=[C:4]1[C:12]1[N:13]=[CH:14][N:15]2[C:20](=[O:21])[N:19]([CH2:22][C:23]#[CH:24])[N:18]=[N:17][C:16]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135985850HCID 135985850, compound

Product 1

HCID 49869138HCID 49869138, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 8 mg, 0.189 mmol, 1.1 eq.) was added in one portion to a slurry of 8-(1H-benzo[d]imidazol-2-yl)-3-(prop-2-ynyl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one (50 mg, 0.172 mmol) in DMF (4.5 mL) at 0° C. and the mixture, which became red, was stirred for 5 minutes before the addition of MeI (21 μL, 0.344 mmol, 2 eq.). The mixture was then stirred overnight and concentrated under high vacuum. The product was absorbed on silica and purified by flash chromatography using DCM:MeCN (80:20) as eluent to give the title compound as a bright yellow/green solid (33 mg, 62% yield). The product was then suspended in ethyl acetate, filtered and washed successively with water, ethyl acetate and diethyl ether to remove any trace of DMF. δH (DMSO-d6): 9.07 (1H, s), 7.76-7.79 (1H, m), 7.67-7.70 (1H, m), 7.35-7.39 (1H, m), 7.29-7.33 (1H, m), 5.17 (2H, d, J=2.5), 4.14 (3H, s), 3.53-3.54 (1H, t, J=2.5).

Workup

  1. concentrationconcentrated under high vacuum
  2. customThe product was absorbed on silica
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8b9dac6417b846d68b2cfb5cd51e0676
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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