1-[(2-Chloroethoxy)methyl]-5-methyl-2,4(1H,3H)-pyrimidinedione → Ethanethioic acid, S-[2-[[-5-methyl-2,4(1H,3H)-pyrimidinedione-1-yl]methoxy]ethyl] ester

HRID 889855Notes

Reaction equation

HRID 889855 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]1=[O:14].[C:15]([O-:18])(=[S:17])[CH3:16].[K+]>CC(C)=O>[C:15](=[O:18])([S:17][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]1=[O:14])[CH3:16]

Participants

4

Reactant 2

HCID 148430571-[(2-Chloroethoxy)methyl]-5-methyl-2,4(1H,3H)-pyrimidinedioneHCID 23670855Potassium ethanethioate

Product 1

HCID 131725267Ethanethioic acid, S-[2-[[-5-methyl-2,4(1H,3H)-pyrimidinedione-1-yl]methoxy]ethyl] esterYield 67.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

92.0 mg (421 μmol) 1-[(2-chloroethoxy)methyl]-5-methyl-2,4(1H,3H)-pyrimidinedione were suspended in 6 ml acetone and 60.1 mg (526 μmol) potassium thioacetate were added and the reaction mixture was heated to reflux for 6 hours. The suspension was concentrated in vacuo and ethyl acetate was added. The organic layer was washed with water, dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography on silica gel (ethyl acetate/hexane 9:1) to give 73 mg of the desired product. MS (ISP): 259.1 (MH+), 281.1 (MNa+). 1H-NMR (DMSO-d6): 1.76 (d, 3H), 2.32 (s, 3H), 3.01 (t, 2H), 3.58 (t, 2H), 5.04 (s, 2H), 7.57 (d, 1H), 11.32 (s, br, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. concentrationThe suspension was concentrated in vacuo and ethyl acetate
  4. additionwas added
  5. washThe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude product was purified by flash chromatography on silica gel (ethyl acetate/hexane 9:1)

Sources & evidence

ORD record
ord-6a35c06c86af4042bb1a7eba33f22fe0
Source dataset
uspto-grants-2006_02
Patent number
US06995143B2

Reaction notes

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