Bromine → HCID 59469373, compound

HRID 1719083Notes

Reaction equation

HRID 1719083 reaction equation
C([O-])(=O)C.[Na+].[F:6][CH:7]([C:9]1[N:10]=[C:11]([CH2:31][CH2:32][CH3:33])[N:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([C:29]#[N:30])=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)[C:13](=[O:15])[CH:14]=1)[CH3:8].[Br:34]Br>C(O)(=O)C>[Br:34][C:14]1[C:13](=[O:15])[N:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([C:29]#[N:30])=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)[C:11]([CH2:31][CH2:32][CH3:33])=[N:10][C:9]=1[CH:7]([F:6])[CH3:8]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 59469459HCID 59469459, compound

Product 1

HCID 59469373HCID 59469373, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of sodium acetate (1.2 g) and 4′-{[4-(1-fluoroethyl)-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile (5 g) in acetic acid (50 mL) was added bromine (0.72 mL), and the mixture was stirred for 4 hr. Acetic acid was removed in vacuo, and the mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale yellow solid (5 g, 83%).

Workup

  1. customAcetic acid was removed in vacuo
  2. additionthe mixture was diluted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a32e50c8f3794acf999e7009a78caa3f
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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