Benzyl Bromide → HCID 58487941, compound

HRID 2382927Notes

Reaction equation

HRID 2382927 reaction equation
[F:1][C:2]1[C:3](=[NH:20])[NH:4][C:5](=[O:19])[N:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:27]([N:4]1[C:3](=[NH:20])[C:2]([F:1])=[CH:7][N:6]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)(=[O:10])=[O:9])[C:5]1=[O:19])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178492822HCID 178492822, compound

Product 1

HCID 58487941HCID 58487941, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 20 mL microwave vial, 5-fluoro-4-imino-1-(4-methoxyphenylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one (111 mg, 0.37 mmol) was stirred at room temperature in dimethyl formamide (3 mL) together with anhydrous potassium carbonate (210 mg, 0.55 mmol). Benzylbromide (89 μL, 0.75 mmol) was added. The reaction was capped and placed on a Biotage Initiator microwave reactor for 20 min at 130° C., with external IR-sensor temperature monitoring from the side of the vessel. 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 3-benzyl-5-fluoro-4-imino-1-(4-methoxyphenylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one as a pale yellow oil (15 mg; 11%): 1H NMR (400 MHz, CDCl3) δ 8.09-8.02 (m, 3H), 7.38-7.27 (m, 6H), 7.00-6.96 (m, 2H), 4.65 (d, J=5.7 Hz, 2H), 3.87 (s, 3H). ESIMS m/z 391 ([M+H]+).

Workup

  1. customThe reaction was capped
  2. washwashed with water (H2O; 3×100 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customPurification by flash chromatography (SiO2, EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-868ecbacecad42388ed17887f7b73c67
Source dataset
uspto-grants-2012_09
Patent number
US08263603B2

Reaction notes

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