Sodium hydride → HCID 66776516, compound

HRID 1616096Notes

Reaction equation

HRID 1616096 reaction equation
[S:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][NH:3]1.[H-].[Na+].[F:11][C:12]([F:16])([F:15])[CH2:13]I>CN(C)C=O>[F:11][C:12]([F:16])([F:15])[CH2:13][S:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 1269845Thiouracil

Product 1

HCID 66776516HCID 66776516, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To solution of 2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (14 g, 0.109 mol) in dimethylformamide (300 mL) was added NaH (13.1 g, 0.327 mol). When the addition was complete, the solution was stirred at 40° C. for 1.5 hours, and 2,2,2-trifluoroethyliodide (27.4 g, 0.131 mol) was added to the solution. The reaction was stirred at 40° C. for 3 hours. The solvent was removed and the residue was poured into water, the mixture was adjusted to pH 3-4 with dilute HCl and extracted with ethyl acetate, the organic layer was dried over Na2SO4 and concentrated under reduced pressure to give 2-(2,2,2-trifluoroethylsulfanyl)-3H-pyrimidin-4-one (26 g, crude) as solid.

Workup

  1. additionWhen the addition
  2. stirringThe reaction was stirred at 40° C. for 3 hours
  3. customThe solvent was removed
  4. additionthe residue was poured into water
  5. extractionextracted with ethyl acetate
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8cc6b5b558284e22b10b6c756cc30bae
Source dataset
uspto-grants-2014_07
Patent number
US08765774B2

Reaction notes

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