Potassium Carbonate → 3-(3-bromo-2-methylphenyl)-1-(4-methoxybenzyl)-5-(phenylselanyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 523275Notes

Reaction equation

HRID 523275 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][NH:8][CH2:9][CH:10]([Se:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([O:13]C)=O)=[CH:5][CH:4]=1.[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]=[C:32]=[O:33])[C:26]=1[CH3:34].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:24][C:25]1[C:26]([CH3:34])=[C:27]([N:31]2[C:11](=[O:13])[CH:10]([Se:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:9][N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=3)[C:32]2=[O:33])[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 655423311-Bromo-3-isocyanato-2-methyl-benzeneHCID 131735565Methyl 3-((4-methoxybenzyl)amino)-2-(phenylselanyl)propanoate

Product 1

HCID 1317355643-(3-bromo-2-methylphenyl)-1-(4-methoxybenzyl)-5-(phenylselanyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 3-((4-methoxybenzyl)amino)-2-(phenylselanyl)propanoate (3.68 g, 9.73 mmol), 1-bromo-3-isocyanato-2-methylbenzene (2.27 g, 10.7 mmol), and K2CO3 (0.672 g, 4.86 mmol) in DMF (49 mL) was heated at 65° C. for 5 h. The cooled mixture was partitioned between water and EtOAc. And the organic phase was washed with brine, dried and concentrated to provide 3-(3-bromo-2-methylphenyl)-1-(4-methoxybenzyl)-5-(phenylselanyl)dihydropyrimidine-2,4(1H,3H)-dione as a light brown solid (5.43 g), used without further purification. Mass spectrum m/z 557, 559, 561 (M+H)+.

Workup

  1. customThe cooled mixture was partitioned between water and EtOAc
  2. washAnd the organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dd5e608dd5e14da5b460b494d4df9f1b
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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