3-Chlorobenzaldehyde → (E)-3-(4-(3-chlorostyryl)-3-methyl-5-nitro-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)propyl acetate

HRID 60346Notes

Reaction equation

[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]([N+:15]([O-:17])=[O:16])=[C:11]([CH3:18])[N:10]([CH3:19])[C:9]1=[O:20])(=[O:3])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.C([O-])(=O)C.[Na+]>CC(O)=O.CC(=O)OCC.O>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]([N+:15]([O-:17])=[O:16])=[C:11](/[CH:18]=[CH:25]/[C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([Cl:21])[CH:23]=2)[N:10]([CH3:19])[C:9]1=[O:20])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 3-(3,4-dimethyl-5-nitro-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)propyl acetate (300 mg, 1.05 mmol) in HOAc (0.7 mL) was added 3-chlorobenzaldehyde (221 mg, 1.58 mmol) and sodium acetate (431 mg, 5.26 mmol). The reaction was heated at 150° C. for 7 h, cooled to RT then diluted with EA (20 mL) and water (20 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by chromatography PE/EA (5:1 to 2:1) to give (E)-3-(4-(3-chlorostyryl)-3-methyl-5-nitro-2,6-dioxo-2,3-dihydropyrimidin-1 (6H)-yl)propyl acetate (70 mg, 16.4% yield) as a brown oil. LCMS: MH+ 408 and TR=1.560 min.

Workup

temperaturecooled to RT
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated to a residue which
customwas purified by chromatography PE/EA (5:1 to 2:1)

Sources & evidence

ORD record: ord-73ae42e1c7ef4f7c8a566c353bffeafc
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440983B2

Reaction notes

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