5-Bromouracil → HCID 83381321, compound

HRID 1943217Notes

Reaction equation

HRID 1943217 reaction equation
Br[C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[SH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][S:10][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1)[CH3:16]

Participants

6

Reactant 3

HCID 58025-BromouracilHCID 11430Potassium CarbonateHCID 12185Ethyl Thioglycolate

Product 1

HCID 83381321HCID 83381321, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-2,4(1H,3H)-pyrimidinedione (15 g, 79 mmol) and ethyl mercaptoacetate (8.58 ml, 79 mmol) in DMF (200 mL) was treated with tetrabutylammonium hydrogen sulfate (6.67 g, 19.64 mmol) and potassium carbonate (23.88 g, 173 mmol) and stirred at ambient temperature overnight. The solution was filtered and concentrated under reduced pressure to yield crude title compound as a yellow oil which foams up under reduced pressure.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7442687c66d942398d8730799384f3f6
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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