Methyl iodide → HCID 17968223, compound

HRID 271585Notes

Reaction equation

HRID 271585 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[CH2:30][CH2:29][C:19]2([NH:23][C:22](=[O:24])[N:21]([CH2:25][CH2:26][CH3:27])[C:20]2=[O:28])[CH2:18][CH2:17]1.[H-].[Na+].[CH3:35]I>CN(C=O)C>[CH3:32][C:2]([CH3:31])([CH3:1])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[CH2:17][CH2:18][C:19]2([N:23]([CH3:35])[C:22](=[O:24])[N:21]([CH2:25][CH2:26][CH3:27])[C:20]2=[O:28])[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 17968209HCID 17968209, compound

Product 1

HCID 17968223HCID 17968223, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2,2-dimethyl-propyl)-6-(2,4-dioxo-3-propyl-1,3,8-triaza-spiro[4.5]dec-8-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.2 g, 0.48 mmol) in DMF (2 ml), NaH (22 mg, 0.55 mmol) and MeI (50 □1, 0.55 mmol) are added at 0° C. The reaction mixture is stirred at ambient temperature for 4 h, quenched with saturated ammonium chloride and extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and filtrated The combined extracts are concentrated and the residue is purified by column chromatography on silica gel using CH2Cl2:MeOH=25:1 (v/v) and CH2Cl2:MeOH=15:1 (v/v) to give 71 mg of desired product in 34% yield.

Workup

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with AcOEt
  3. washThe organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated The combined extracts
  6. concentrationare concentrated
  7. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b59cca17a5634d998c8b2e20e1f7162a
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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