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

HRID 2210907Notes

Reaction equation

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

Participants

Reactant 5

HCID 176Acetic Acid

HCID 8028Tetrahydrofuran3×

HCID 13436Diphenyl disulfide

HCID 2724682Lithium diisopropylamide

HCID 186710321-Butyl-5-ethyluracil

Product 1

HCID 545239331-Butyl-5-ethyl-6-phenylthiouracilYield 7%

Conditions

Temperature: -25 °C

Procedure

Then, a solution of 4.4 mmol of lithium diisopropylamide in 2.8 ml of tetrahydrofuran was added dropwise to a solution of 392 mg (2.0 mmol) 1-butyl-5-ethyluracil in 9 ml of tetrahydrofuran under a nitrogen atmosphere at -70° C. and stirred for 70 minutes at -70° C. and further 5 minutes at -25° C. The mixture was cooled to -70° C. again, added with a solution of 567 mg (2.6 mmol) diphenyl disulfide in 3 ml of tetrahydrofuran, stirred for 20 minutes, added with 1 ml of acetic acid, brought to room temperature, washed with saturated aqueous solution of sodium chloride and concentrated under reduced pressure. The residue was adsorbed on a silica gel, eluted with 10% ethyl acetate/hexane and crystallized from hexane to obtain 40 mg of 1-butyl-5-ethyl-6-phenylthiouracil (Yield: 7%).

Workup

temperatureThe mixture was cooled to -70° C. again
stirringstirred for 20 minutes
custombrought to room temperature
washwashed with saturated aqueous solution of sodium chloride
concentrationconcentrated under reduced pressure
washeluted with 10% ethyl acetate/hexane
customcrystallized from hexane

Sources & evidence

ORD record: ord-f116e2130b8a44fabf4625baf11c0e65
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05461060

Reaction notes

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