Methanol → HCID 12051690, compound

HRID 2305993Notes

Reaction equation

HRID 2305993 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[C:8](=[O:14])[NH:9][C:10]([SH:13])=[N:11][CH:12]=2)=[CH:4][CH:3]=1.[CH3:17]O>[H-].[Na+]>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[C:8](=[O:14])[NH:9][C:10]([S:13][CH3:17])=[N:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 178518763HCID 178518763, compound

Product 1

HCID 12051690HCID 12051690, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 24758Sodium hydrideSolvent

Conditions

Temperature
60 °C

Procedure

Idomethane (Aldrich) (2.8 mL. 45 mmoles) was added to a solution of 5-(4-chlorophenoxy)-2-(mercapto)pyrimidine-4(3H)-one (10.24 g, 40 mmoles) in methanol (52 mL) and 1.0 N aqueous sodium hydride (40 mL). The resultant mixture was stirred at ambient temperature for 5.5 hours, then heated at 60° C. for 30 minutes. The mixture was spin evaporated in vacuo to give a solid, which was triturated with ice-water and then collected by suction filtration. Half of the light brown solid was recrystallized from ethyl acetate and half from ethanol to give 7.06 g (88% yield) of 5-(4-chlorophenoxy)-2(methylmercapto)pyrimidin-4-(3H)-one as a fluffy off-white solid, mp 232-233° C.

Workup

  1. customevaporated in vacuo
  2. customto give a solid, which
  3. customwas triturated with ice-water
  4. filtrationcollected by suction filtration
  5. customHalf of the light brown solid was recrystallized from ethyl acetate and half from ethanol

Sources & evidence

ORD record
ord-39a5d2bba8364d0b88488091dac26620
Source dataset
uspto-grants-2002_08
Patent number
US06440965B1

Reaction notes

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