Methyl iodide → HCID 19014334, compound

HRID 1728555Notes

Reaction equation

HRID 1728555 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:19])[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[N:7]=1.[OH-].[K+].[CH3:22]I>C(O)C>[CH3:1][C:2]1[N:3]([CH3:22])[C:4](=[O:19])[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 14797Potassium Hydroxide2×HCID 136199683HCID 136199683, compound

Product 1

HCID 19014334HCID 19014334, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,5,6-trimethyl-7-phenyl-3H,7H-pyrrolo-[2,3-d]pyrimidin-4-one (1.46 g, 5.8 mM) (N S Girgis et atl, Synthesis, 1985, p101-104). A mixture of potassium hydroxide flake (327 mg, 5.8 mM) and methyl iodide (0.54 ml, 8.7 mM) in ethanol (37 ml) was heated under reflux for 15 hours. A mixture of methyl iodide (0.5 ml) and potassium hydroxide flake (0.3 g) was added and the reaction mixture heated under reflux for a further 3 hours. The solvent was evaporated and the residual solid suspended in water. The solid was collected by filtration and washed with water to give 2,3,5,6-tetramethyl-7-phenyl-3H,7H-pyrrolo-[2,3-d]pyrimidin-4-one (1.21 g, 78.5% yield) as a light foam solid, m p 215°-217° C.; NMR: DMSO-d6 2.0-2.1(3H, s, CH3), 2.3(3H, s, pyrrole CH3), 2.4(3 H, s, pyrrole- CH3), 3.4-3.5(3H, s, N--CH3), 7.3-7.6(5H, complex, aromatic).

Workup

  1. customN S Girgis et atl, Synthesis, 1985
  2. temperaturewas heated
  3. temperatureunder reflux for 15 hours
  4. additionwas added
  5. temperaturethe reaction mixture heated
  6. temperatureunder reflux for a further 3 hours
  7. customThe solvent was evaporated
  8. filtrationThe solid was collected by filtration
  9. washwashed with water

Sources & evidence

ORD record
ord-ef9735209e4342e59842665111c513c4
Source dataset
uspto-grants-1994_07
Patent number
US05328910

Reaction notes

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