Diethyl Ether → 1,3-Dimethyl-6-[2-(dimethylamino)vinyl]-5-nitrouracil

HRID 467846Notes

Reaction equation

HRID 467846 reaction equation
[CH3:1][N:2]1[C:9]([CH3:10])=[C:8]([N+:11]([O-:13])=[O:12])[C:6](=[O:7])[N:5]([CH3:14])[C:3]1=[O:4].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19].C(OCC)C>CN(C)C=O>[CH3:1][N:2]1[C:9]([CH:10]=[CH:17][N:18]([CH3:20])[CH3:19])=[C:8]([N+:11]([O-:13])=[O:12])[C:6](=[O:7])[N:5]([CH3:14])[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 78373Dimethylformamide dimethyl acetalHCID 7503695-Nitro-1,3,6-trimethyluracil2×

Product 1

HCID 10834761,3-Dimethyl-6-[2-(dimethylamino)vinyl]-5-nitrouracil

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Step 1 intermediate, 1,3,6-Trimethyl-5-nitrouracil (0.60 g, 3.012 mmol) in dry N,N-dimethylformamide (5.0 mL) was added N,N-dimethylformamide dimethyl acetal (0.53 g, 4.447 mmol) and the reaction mixture was stirred at room temperature for 2 h. After this time, diethyl ether was added to the reaction mixture and the precipitate was collected by filtration and washed with diethyl ether to give 0.45 g of the product as brownish solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 2.98 (s, 6H), 3.16 (s, 3H), 3.40 (s, 3H), 4.78 (d, J=12.6 Hz, 1H), 7.05 (d, J=12.6 Hz, 1H); APCI-MS (m/z) 255.11 (M+H)+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-04834454b76448e1ac6b1a865c0589c4
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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