1,4-Dioxane → 1,2,3,4-Tetrahydro-2,4-dioxo-1-(4-oxobutyl)-5-pyrimidinecarbonitrile

HRID 12686Notes

Reaction equation

HRID 12686 reaction equation
C(O[C:4](OCC)([CH3:17])[CH2:5][CH2:6][N:7]1[CH:12]=[C:11]([C:13]#[N:14])[C:10](=[O:15])[NH:9][C:8]1=[O:16])C.[O:21]1CCOCC1>>[O:16]=[C:8]1[NH:9][C:10](=[O:15])[C:11]([C:13]#[N:14])=[CH:12][N:7]1[CH2:6][CH2:5][CH2:4][CH:17]=[O:21]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 686958921-(3,3-Diethoxy-butyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile

Product 1

HCID 589942301,2,3,4-Tetrahydro-2,4-dioxo-1-(4-oxobutyl)-5-pyrimidinecarbonitrile

Conditions

Temperature
60 °C

Procedure

1-(3,3-Diethoxy-butyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile (Prep 54, 200 mg, 0.71 mmol) was dissolved in dioxane (8 mL) and 1N HClaq (1 mL) was added. The mixture was warmed at 60° C. for 20 minutes. The solvents were evaporated, the residue was submitted to lyophilization, to give 150 mg of the title compound that was used in the next step without further purification (quantitative yield).

Workup

  1. addition1N HClaq (1 mL) was added
  2. customThe solvents were evaporated

Sources & evidence

ORD record
ord-aed69bfe41c4432fba303d31b332e3f4
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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