Sodium Acetate → (E)-3-(3-methyl-5-nitro-2,6-dioxo-4-(3-(trifluoromethoxy)styryl)-2,3-dihydro pyrimidin-1(6H)-yl)propyl acetate

HRID 60342Notes

Reaction equation

[CH3:1][N:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[C:5](=[O:12])[N:4]([CH2:13][CH2:14][CH2:15][O:16][CH:17]2[CH2:22]CCC[O:18]2)[C:3]1=[O:23].[F:24][C:25]([F:36])([F:35])[O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH:30]=O.C([O-])(=O)C.[Na+]>CC(O)=O.CC(=O)OCC.O>[C:17]([O:16][CH2:15][CH2:14][CH2:13][N:4]1[C:5](=[O:12])[C:6]([N+:9]([O-:11])=[O:10])=[C:7](/[CH:8]=[CH:30]/[C:29]2[CH:32]=[CH:33][CH:34]=[C:27]([O:26][C:25]([F:24])([F:35])[F:36])[CH:28]=2)[N:2]([CH3:1])[C:3]1=[O:23])(=[O:18])[CH3:22]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 1,6-dimethyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrimidine-2,4(1H,3H)-dione (1 g, 3.05 mmol) in HOAc (4 mL) was added 3-(trifluoromethoxy)benzaldehyde (0.755 g, 3.97 mmol) and sodium acetate (0.752 g, 9.16 mmol). The reaction was heated at 140° C. for 6 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-(3-methyl-5-nitro-2,6-dioxo-4-(3-(trifluoromethoxy)styryl)-2,3-dihydropyrimidin-1(6H)-yl)propyl acetate (200 mg, 14.3% yield) as a brown oil. LCMS: MH+ 458 and TR=1.689 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-6e07e077f946466f856b0301af2c7dd7
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440983B2

Reaction notes

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