Potassium Carbonate → 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)-4-Fluorobenzonitrile

HRID 2065563Notes

Reaction equation

HRID 2065563 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([Cl:9])[NH:4][C:3]1=[O:10].Br[CH2:12][C:13]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[Cl:9][C:5]1[N:4]([CH2:12][C:13]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:14]=2[C:15]#[N:16])[C:3](=[O:10])[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 961416-chloro-3-methylpyrimidine-2,4(1H,3H)-dioneHCID 219849902-(Bromomethyl)-4-fluorobenzonitrile

Product 1

HCID 230893582-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)-4-FluorobenzonitrileYield 60%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of crude 3-methyl-6-chlorouracil (0.6 g, 3.8 mmol), 2-bromomethyl-4-fluorobenzonitrile (0.86 g, 4 mmol) and K2CO3 (0.5 g, 4 mmol) in DMSO (10 mL) was stirred at 60° C. for 2 hours. The reaction was diluted with water and extracted with EtOAc. The organics were dried over MgSO4 and the solvent removed. The residue was purified by column chromatography. 0.66 g of the product was obtained (yield: 60%). 1H-NMR (400 MHz, CDCl3): δ 7.73 (dd, J=7.2, 8.4 Hz, 1H), 7.26 (d, J=4.0 Hz, 1H), 7.11-7.17 (m, 1H), 6.94 (dd, J=2.0, 9.0 Hz, 1H), 6.034 (s, 2H), 3.39 (s, 3H). MS (ES) [m+H] calc'd for C13H9ClFN3O2, 293.68. found 293.68.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organics were dried over MgSO4
  3. customthe solvent removed
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-94c254d66886493493312e679b3f4e7e
Source dataset
uspto-grants-2012_10
Patent number
US08288539B2

Reaction notes

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