Dimethylformamide → HCID 58487938, compound

HRID 2382926Notes

Reaction equation

HRID 2382926 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:4](=[O:18])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.I[CH2:31][CH3:32]>C(OCC)(=O)C>[C:12]1([S:9]([N:5]2[CH:6]=[C:7]([F:8])[C:2](=[NH:1])[N:3]([CH2:31][CH3:32])[C:4]2=[O:18])(=[O:10])=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 58138399HCID 58138399, compound

Product 1

HCID 58487938HCID 58487938, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a 25 mL sealed tube were added 4-amino-1-benzenesulfonyl-5-fluoro-1H-pyrimidine-2-one (1.0 g, 3.71 mmol), anhydrous potassium carbonate (K2CO3; 2.05 g, 14.9 mmol), and N,N-dimethylformamide (DMF; 10 mL), followed by iodoethane (EtI; 3.45 g, 22.3 mmol). The reaction vessel was sealed, and the reaction mixture was warmed to 60° C. and stirred for 1 hour. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (EtOAc; 250 mL), and washed with water (H2O; 3×100 mL). The organic phase was dried over magnesium sulfate (MgSO4), filtered, and the solvent evaporated under reduced pressure. Purification by flash chromatography (SiO2, EtOAc/Hexanes gradient) afforded benzenesulfonyl-5-fluoro-4-imino-3-ethyl-3,4-dihydro-1H-pyrimidin-2-one as a pale yellow solid (200 mg; 18%): mp 163-166° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.82 (m, 1H), 8.29 (d, J=6.8 Hz, 1H), 8.02 (dd, J=8.4, 1.1 Hz, 2H), 7.79 (ddd, J=6.9, 2.3, 1.1 Hz, 1H), 7.66 (dd, J=10.7, 4.9 Hz, 2H), 3.31 (q, J=7.2 Hz, 2H), 1.09 (t, J=7.2 Hz, 3H); ESIMS m/z 298 ([M+H]+).

Workup

  1. customTo a 25 mL sealed tube
  2. customThe reaction vessel was sealed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washwashed with water (H2O; 3×100 mL)
  5. dry with materialThe organic phase was dried over magnesium sulfate (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customPurification by flash chromatography (SiO2, EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-6fa13224a5f04d8e80ce0ea676f3fd23
Source dataset
uspto-grants-2012_09
Patent number
US08263603B2

Reaction notes

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