Dimethylformamide → 5-fluoro-4-imino-1-(4-methoxyphenylsulfonyl)-3-methyl-3,4-dihydropyrimidin-2(1H)-one

HRID 631839Notes

Reaction equation

HRID 631839 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:4](=[O:20])[N:3]=1.[C:21](=O)([O-])[O-].[K+].[K+].CN(C)C=O.IC>CCOC(C)=O>[F:8][C:7]1[C:2](=[NH:1])[N:3]([CH3:21])[C:4](=[O:20])[N:5]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)(=[O:10])=[O:11])[CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 581384004-Amino-5-fluoro-1-(4-methoxyphenylsulfonyl)pyrimidin-2(1H)-one

Product 1

HCID 584879375-fluoro-4-imino-1-(4-methoxyphenylsulfonyl)-3-methyl-3,4-dihydropyrimidin-2(1H)-oneYield 12%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To an 8-mL screw capped vial were added 4-amino-5-fluoro-1-(4-methoxyphenylsulfonyl)pyrimidin-2(1H)-one (0.293 g, 0.979 mmol), anhydrous potassium carbonate (K2CO3; 0.271 g, 1.96 mmol), and N,N-dimethylformamide (DMF; 4 mL), followed by iodomethane (CH3I; 0.208 g, 1.47 mmol). The reaction vessel was sealed, and the reaction mixture was warmed to 60° C. and stirred for 4 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (20 mL), and washed with water (H2O; 3×10 mL). The organic phase was dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure. Purification by flash chromatography (silica gel (SiO2), EtOAc/Hexanes gradient) afforded the title compound as a pale yellow solid (36 milligrams (mg), 12%): mp 158-162° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.01 (d, J=9.22 Hz, 2H), 7.74 (d, J=5.27 Hz, 1H), 7.04 (d, J=9.23 Hz, 2H), 3.90 (s, 3H), 3.31 (s, 3H); ESIMS m/z 314 ([M+H]+).

Workup

  1. customTo an 8-mL screw capped vial
  2. customThe reaction vessel was sealed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washwashed with water (H2O; 3×10 mL)
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customPurification by flash chromatography (silica gel (SiO2), EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-b543bdd00a584974887269ecdf70c7a9
Source dataset
uspto-grants-2016_04
Patent number
US09321734B2

Reaction notes

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