1-(3,3-Diethoxy-propyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile → 2,4-Dioxo-1-(3-oxo-propyl)-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile

Reaction equation

C([O:3][CH:4](OCC)[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>O1CCOCC1>[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][CH:4]=[O:3]

Participants

Conditions

Temperature: 60 °C

Procedure

1-(3,3-diethoxy-propyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile (Prep 34, 50 mg, 0.21 mmol) was dissolved in dioxane (5 mL) and 1N HClaq (500 μl) was added. The mixture was warmed at 60° C. for 15 minutes. The solvents were evaporated and the residue submitted to liophilization to give 53 mg of the title compound (quantitative yield).

Workup

addition1N HClaq (500 μl) was added
customThe solvents were evaporated

Sources & evidence

ORD record: ord-ee4295b20e334f398cc183b168edb499
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727988B2

Reaction notes

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Participants

Reactant 1

HCID 589941901-(3,3-Diethoxy-propyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile

Product 1

HCID 589942042,4-Dioxo-1-(3-oxo-propyl)-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrileYield 130.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent