Dimethylformamide dimethyl acetal → 6-(2-(dimethylamino)vinyl)-1-methyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrimidine-2,4(1H,3H)-dione

HRID 60354Notes

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][CH2:21][CH2:20][CH2:19][O:18]2)[C:3]1=[O:23].[CH3:24][N:25]([CH:27](OC)OC)[CH3:26]>CN(C=O)C>[CH3:24][N:25]([CH3:27])[CH:26]=[CH:8][C:7]1[N:2]([CH3:1])[C:3](=[O:23])[N:4]([CH2:13][CH2:14][CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:5](=[O:12])[C:6]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 95 °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 (980 mg, 3 mmol) in DMF (2 mL) was added DMF-DMA (5 mL). The reaction was heated at 95° C. for 15 h, cooled to RT and concentrated to a residue which was dissolved in EA (20 mL). The mixture was washed with aq. 1N LiCl (3×10 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (2:1) to give 6-(2-(dimethylamino)vinyl)-1-methyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl) pyrimidine-2,4(1H,3H)-dione (840 mg, 73% yield) as a yellow oil. LCMS: MH+ 383 and TR=1.308 min.

Workup

temperaturecooled to RT
concentrationconcentrated to a residue which
dissolutionwas dissolved in EA (20 mL)
washThe mixture was washed with aq. 1N LiCl (3×10 mL)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated to a residue which
customwas purified by chromatography
washeluted with PE/EA (2:1)

Sources & evidence

ORD record: ord-c6200e610f054f09bc48a076a0c84e1b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440983B2

Reaction notes

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