Bromine → HCID 59469380, compound

HRID 1674420Notes

Reaction equation

HRID 1674420 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][O:7][CH2:8][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.[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[CH2:8][O:7][CH3:6]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 59469513HCID 59469513, compound

Product 1

HCID 59469380HCID 59469380, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of sodium acetate (3.4 g) and 4′-{[4-(methoxymethyl)-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile (15 g) in acetic acid (150 mL) was added bromine (2.1 mL), and the mixture was stirred for 4 hr. Acetic acid was removed in vacuo, and the reaction 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 (7 g, 39%).

Workup

  1. customAcetic acid was removed in vacuo
  2. additionthe reaction 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-d1abb551f14447a48bea292e4e222fd5
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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