Methyl iodide → 2-Amino-5-iodo-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 598186Notes

Reaction equation

HRID 598186 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:13])[C:5]2[C:10]([I:11])=[CH:9][N:8]([CH3:12])[C:6]=2[N:7]=1.[H-].[Na+].I[CH3:17]>CN(C)C=O.O>[NH2:1][C:2]1[N:3]([CH3:17])[C:4](=[O:13])[C:5]2[C:10]([I:11])=[CH:9][N:8]([CH3:12])[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136400718HCID 136400718, compound

Product 1

HCID 672673352-Amino-5-iodo-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-oneYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-iodo-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (15.4 g, 53.1 mmol) in N,N-dimethylformamide (150 ml) was added sodium hydride (66% dispersion in oil, 1.93 g, 53.1 mmol) and iodomethane (3.31 ml, 53.1 mmol) at 0° C., and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was diluted with water and extracted with ethyl acetate (×2) and ethyl acetate-tetrahydrofuran (×2). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 50-100% hexane/ethyl acetate gradient mixture, and the desired fractions were concentrated in vacuo. The residual crystals were washed with diethyl ether to give 12.3 g (76%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate (×2) and ethyl acetate-tetrahydrofuran (×2)
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with a 50-100% hexane/ethyl acetate gradient mixture
  6. concentrationthe desired fractions were concentrated in vacuo
  7. washThe residual crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-ea3bfd8d15c94bc883cf6d5861953a97
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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