N-bromobutanimide → Methyl 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate

HRID 1926903Notes

Reaction equation

HRID 1926903 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:17][O:16][C:12]=2[N:13]=[CH:14][N:15]=1.[Br:28]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([Br:28])[O:16][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 25124063Methyl 6-{[5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate

Product 1

HCID 58016901Methyl 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Dissolve 4.1 g (11.1 mmol) 6-{[5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester at room temperature in 150 ml carbon tetrachloride and add 2.2 g (12.2 mmol) N-bromosuccinimide. Stir the mixture under reflux for three hours, then filter after cooling to room temperature and concentrate the filtrate by vacuum evaporation. 4.8 g (96% of theor.) of the title compound is obtained.

Workup

  1. temperatureunder reflux for three hours
  2. filtrationfilter
  3. concentrationconcentrate the filtrate
  4. customby vacuum evaporation

Sources & evidence

ORD record
ord-a45be306e9c948ac8761892fa3688442
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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