Dimethylformamide → HCID 67123488, compound

HRID 1843132Notes

Reaction equation

HRID 1843132 reaction equation
[OH:1][CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[NH:12][C:11]2[C:6]1=[N:7][C:8]([C:15]1[CH:16]=[N:17][N:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=13)=[N:9][CH:10]=2)[CH3:4].[CH3:26]N(C=O)C.CI>>[OH:1][CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[N:12]([CH3:26])[C:11]2[C:6]1=[N:7][C:8]([C:15]1[CH:16]=[N:17][N:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=13)=[N:9][CH:10]=2)[CH3:4]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 67124182HCID 67124182, compound

Product 1

HCID 67123488HCID 67123488, compoundYield 29%

Procedure

To a solution of example 28 (20 mg, 0.06 mmol) in AcN (2 mL) and DMF (0.5 mL) silver (I) oxide (23 mg, 0.12 mmol) and methyl iodide (0.005 mL, 0.09 mmol) were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered through a plug of Celite® and the solvent was evaporated under reduced pressure. The crude residue was cromatographed on a silica gel flash system (ISCO Combiflash) using CH2Cl2/MeOH mixtures of increasing polarity as eluent to afford 6 mg of the desired product (29% yield).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite®
  2. customthe solvent was evaporated under reduced pressure
  3. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-d79d28c66ce843e6838bd320be857a5a
Source dataset
uspto-grants-2015_02
Patent number
US08946257B2

Reaction notes

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