Acetic Acid → 1-Ethoxymethyl-5-ethyl-6-phenylthiouracil

HRID 2210902Notes

Reaction equation

HRID 2210902 reaction equation
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].[CH2:9]([O:11][CH2:12][N:13]1[CH:20]=[C:19]([CH2:21][CH3:22])[C:17](=[O:18])[NH:16][C:14]1=O)[CH3:10].C1([S:29]SC2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C.O1C[CH2:44][CH2:43][CH2:42]1>C(OCC)(=O)C>[CH2:9]([O:11][CH2:12][N:13]1[C:20]([C:6]2[CH:5]=[CH:7][CH:44]=[CH:43][CH:42]=2)=[C:19]([CH2:21][CH3:22])[C:17](=[O:18])[NH:16][C:14]1=[S:29])[CH3:10]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8028Tetrahydrofuran4×HCID 13436Diphenyl disulfideHCID 2724682Lithium diisopropylamideHCID 102623171-Ethoxymethyl-5-ethyluracil

Product 1

HCID 544610701-Ethoxymethyl-5-ethyl-6-phenylthiouracilYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

Then, 2.2 ml of lithium diisopropylamide (4.4 mmol) solution in tetrahydrofuran (2.1M) was added to 6 ml of tetrahydrofuran under a nitrogen atmosphere at -70° C., to which a solution of 0.40 g (2.0 mmol) of 1-ethoxymethyl-5-ethyluracil in 3 ml of tetrahydrofuran was added dropwise over 15 minutes. After stirring for 1 hour at -70° C., the reaction mixture was added with a solution of 0.57 g of diphenyl disulfide in 2 ml of tetrahydrofuran dropwise over 10 minutes and allowed to react for 30 minutes. The reaction mixture was added with 1 ml of acetic acid, brought to room temperature and then added with 30 ml of ethyl acetate. The mixture was washed with water (3 ml×5) and saturated aqueous solution of sodium hydrogencarbonate (twice), dried on magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexane=3:17) and crystallized from ethyl acetate to obtain 0.61 g of 1-ethoxymethyl-5-ethyl-6-phenylthiouracil (Yield: 32%).

Workup

  1. additionwas added dropwise over 15 minutes
  2. customto react for 30 minutes
  3. custombrought to room temperature
  4. washThe mixture was washed with water (3 ml×5) and saturated aqueous solution of sodium hydrogencarbonate (twice),
  5. customdried on magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane=3:17)
  8. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1dd1befbb0ee4834b3be1dce481e2747
Source dataset
uspto-grants-1995_10
Patent number
US05461060

Reaction notes

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