Methyl iodide → HCID 58938687, compound

HRID 598189Notes

Reaction equation

HRID 598189 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[F:21])=[CH:12][N:11]([CH3:22])[C:9]=2[N:10]=1)[CH2:2][CH3:3].[H-].[Na+].I[CH3:31]>CN(C)C=O>[CH2:25]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:31])=[CH:16][C:15]=3[F:21])=[CH:12][N:11]([CH3:22])[C:9]=2[N:10]=1)[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58938683HCID 58938683, compound

Product 1

HCID 58938687HCID 58938687, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(dipropylamino)-5-(2-fluoro-4-hydroxyphenyl)-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (30 mg, 0.0805 mmol) in N,N-dimethylformamide (0.5 ml) were added sodium hydride (66% dispersion in oil; 3.2 mg, 0.0886 mmol) and iodomethane (0.006 ml, 0.0886 ml) at 0° C., and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was diluted with ice-cold water and extracted with ethyl acetate (×1). The organic layer was washed with water (×1) and brine (×1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 20% hexane/ethyl acetate mixture. The desired fractions were concentrated in vacuo to give 23 mg (74%) of the title compound as an oil.

Workup

  1. additionThe reaction mixture was diluted with ice-cold water
  2. extractionextracted with ethyl acetate (×1)
  3. washThe organic layer was washed with water (×1) and brine (×1)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 20% hexane/ethyl acetate mixture
  8. concentrationThe desired fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-bd37734834e84248be0b29ffb408ce5d
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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