Methyl iodide → HCID 178504026, compound

HRID 1975236Notes

Reaction equation

HRID 1975236 reaction equation
[CH3:1]I.[CH3:3][C:4]([C:7]1[C:12]([OH:13])=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:10]=[C:9]([NH:18][C:19]([NH2:21])=[S:20])[N:8]=1)([CH3:6])[CH3:5]>C(O)C>[CH3:6][C:4]([C:7]1[C:12]([OH:13])=[C:11]([C:14]([CH3:15])([CH3:17])[CH3:16])[N:10]=[C:9]([NH:18][C:19](=[NH:21])[S:20][CH3:1])[N:8]=1)([CH3:3])[CH3:5]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 19101102HCID 19101102, compound

Product 1

HCID 178504026HCID 178504026, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl iodide (1.05 g, 7.4 mmol) is added to an ethanol (50 mL) solution of N-[4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]thiourea (2.0 g, 7.1 mmol) and the mixture is heated at reflux under argon for 2.5 hours. The ethanol is evaporated under reduced pressure and the residue is taken up in 50 mL EtOAc. The EtOAc solution is washed with saturated NaHCO3 (3×50 mL) and 50 mL of brine. Drying over MgSO4 and evaporation of solvent gives an off-white solid. Recrystallization from ether/hexane gives 1.5 g (71%) of N-[4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-S-methyl isothiourea; mp 163°-165° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux under argon for 2.5 hours
  3. customThe ethanol is evaporated under reduced pressure
  4. washThe EtOAc solution is washed with saturated NaHCO3 (3×50 mL) and 50 mL of brine
  5. dry with materialDrying over MgSO4 and evaporation of solvent
  6. customgives an off-white solid
  7. customRecrystallization from ether/hexane

Sources & evidence

ORD record
ord-8e9b2659c0f54808963f881c91a2ffc0
Source dataset
uspto-grants-1994_02
Patent number
US05284949

Reaction notes

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