Methyl iodide → HCID 58464086, compound

HRID 629251Notes

Reaction equation

HRID 629251 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[N:12][C:11]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][N:9]=2)[C:4](=[O:22])[NH:3]1.[H-].[Na+].I[CH3:27]>CN(C=O)C>[CH3:27][N:3]1[C:2]([CH3:23])([CH3:1])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[N:12][C:11]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][N:9]=2)[C:4]1=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58464129HCID 58464129, compound

Product 1

HCID 58464086HCID 58464086, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,4-dimethyl-1-(5-(phenylethynyl)pyrazin-2-yl)tetrahydropyrimidin-2(1H)-one (Example 164, step 2) (30 mg, 0.098 mmol) in 2 ml of DMF was added 60% sodium hydride suspension (4.7 mg, 0.118 mmol, 1.2 equiv.). After stirring at room temperature for 15 min, iodomethane (7.4 ml, 16.7 mg, 0.118 mmol, 1.2 equiv.) was added and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and was worked up with ethyl acetate/water. Flash chromatography over a prepacked 20 g silica column eluting with a heptane to 50% ethyl acetate in heptane gradient yielded the title compound (25.4 mg, 81% yield) as an off-white solid, MS: m/e=321.3 (M+H+).

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washFlash chromatography over a prepacked 20 g silica column eluting with a heptane to 50% ethyl acetate in heptane gradient

Sources & evidence

ORD record
ord-1d50780d677947bfaeae4598c862b2df
Source dataset
uspto-grants-2016_04
Patent number
US09315498B2

Reaction notes

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