Methyl iodide → HCID 90407358, compound

HRID 2277462Notes

Reaction equation

HRID 2277462 reaction equation
[OH:1][CH2:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]([CH3:17])[CH:15]=[N:14][C:13]=3[C:18]3[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][N:19]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4]1.[H-].[Na+].[CH3:28]I>CN(C=O)C>[CH3:28][O:1][CH2:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]([CH3:17])[CH:15]=[N:14][C:13]=3[C:18]3[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][N:19]=3)=[CH:8][CH:7]=2)[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90407600HCID 90407600, compound

Product 1

HCID 90407358HCID 90407358, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(5-{4-[1-(hydroxymethyl)cyclopropyl]phenyl}-1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile (30 mg, 0.09 mmol; Example 17, part A) in anhydrous DMF (2 mL) at 0° C. was added 60% NaH (6 mg, 0.136 mmol). After stirring for 10 minutes, MeI (10 μL, 0.136 mml) was added. The reaction mixture was warmed up to r.t. and stirred for 3 hr. It was then purified by ISCO flash column chromatography (MeOH/DCM=0-5%) to give the title product which was used for next step. [M+H] Calc'd for C21H20N4O, 345. Found, 345.

Workup

  1. stirringstirred for 3 hr
  2. customIt was then purified by ISCO flash column chromatography (MeOH/DCM=0-5%)

Sources & evidence

ORD record
ord-bede5aba30ea491caf3c523cc430c1c6
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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