Methyl iodide → HCID 86604625, compound

HRID 1678051Notes

Reaction equation

HRID 1678051 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:15][C:9]2[N:10]=[CH:11][N:12]=[C:13]([Cl:14])[C:8]=2[C:7]=1[OH:16])=[O:5])C.[H-].[Na+].[CH3:19]I>O1CCCC1>[CH3:1][O:3][C:4]([C:6]1[S:15][C:9]2[N:10]=[CH:11][N:12]=[C:13]([Cl:14])[C:8]=2[C:7]=1[O:16][CH3:19])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86604626HCID 86604626, compound

Product 1

HCID 86604625HCID 86604625, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Chloro-5-hydroxy-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.4 g, 1.5 mmol) in tetrahydrofuran (10 mL) was slowly added to a slurry of sodium hydride (60 percent in mineral oil, 0.1 g 2.5 mmol) in tetrahydrofuran (30 mL) and stirred for one hour. Methyl iodide (2 mL) was added and the solution warmed to reflux for two hours. After cooling the reaction was quenched with water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine, dried (NaSO4) and concentrated. The residue was purified by chromatography over silica (40 percent ethyl acetate/hexane) affording product as a yellow solid. (0.2 g, 50 percent) yield.

Workup

  1. temperaturethe solution warmed
  2. temperatureto reflux for two hours
  3. temperatureAfter cooling the reaction
  4. customwas quenched with water (100 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (NaSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography over silica (40 percent ethyl acetate/hexane)
  10. customaffording product as a yellow solid
  11. custom(0.2 g, 50 percent) yield

Sources & evidence

ORD record
ord-00e9b99d3c134f89a48e82d34837830d
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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