Methyl iodide → HCID 70817500, compound

HRID 82283Notes

Reaction equation

HRID 82283 reaction equation
[I:1][C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[N:4]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])[CH:3]=1.[H-].[Na+].[CH3:18]I>C1COCC1>[I:1][C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[N:4]([C:11]([CH3:15])([CH3:14])[CH2:12][O:13][CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 708175262-(5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropan-1-ol

Product 1

HCID 70817500HCID 70817500, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

An anhydrous THF (100 mL) solution of 2-(5-Iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methyl-propan-1-ol (Preparation 22) (32 g, 100.91 mmol) was added slowly to a suspension of NaH (60% in paraffin oil, 2.98 g, 121.13 mmol) in anhydrous THF (200 mL) at 00° C. under nitrogen. The mixture was warmed to room temperature and stirred for another 30 minutes and again cooled to 00° C. and methyl iodide (19 mL, 302.82 mmol) was added drop wise. The reaction mixture was stirred at room temperature for 2 hours, quenched with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulphate and evaporated to dryness in vacuo. The crude material was purified by column chromatography on silica (100-200 mesh, gradient of hexane:EtOAc 100:0 to 70:30) to afford the title compound as a yellow sticky solid in 22% yield, 7.5 g.

Workup

  1. temperatureagain cooled to 00° C
  2. stirringThe reaction mixture was stirred at room temperature for 2 hours
  3. customquenched with aqueous saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness in vacuo
  8. customThe crude material was purified by column chromatography on silica (100-200 mesh, gradient of hexane:EtOAc 100:0 to 70:30)

Sources & evidence

ORD record
ord-4cfe5bdb8554497588576aeca7a76f5f
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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