2-Bromopyrimidine → HCID 53634998, compound

HRID 2416717Notes

Reaction equation

HRID 2416717 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:29]=[CH:28][C:16]2[CH2:17][CH:18]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:19](=[O:22])[NH:20][CH2:21][C:15]=2[CH:14]=1.Br[C:31]1[N:36]=[CH:35][CH:34]=[CH:33][N:32]=1.C([O-])(O)=O.[Na+]>CCO>[N:32]1[CH:33]=[CH:34][CH:35]=[N:36][C:31]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:29]=[CH:28][C:16]2[CH2:17][CH:18]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:19](=[O:22])[NH:20][CH2:21][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 783452-BromopyrimidineHCID 516892Sodium BicarbonateHCID 131724662HCID 131724662, compound

Product 1

HCID 53634998HCID 53634998, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl (±)-8-(3-amino-1-propyloxy)-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate trifluoroacetate salt (0.75 g, 2 mmol), 2-bromopyrimidine (0.5 g, 3 mmol), NaHCO3 (1.4 g, 17 mmol), and EtOH (10 mL) was heated to reflux. After 24 hr, the mixture was filtered and the insoluble material was washed with MeOH. The filtrate and washings were combined and concentrated, and the residue was purified by chromatography on silica gel (1%-6% MeOH/CH2Cl2) to give the title compound (0.54 g, 82%) as a white foam: MS (ES) m/e 385.5 (M+H)+.

Workup

  1. temperaturewas heated to reflux
  2. filtrationthe mixture was filtered
  3. washthe insoluble material was washed with MeOH
  4. concentrationconcentrated
  5. customthe residue was purified by chromatography on silica gel (1%-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b83e6f1e23b6479689905dbe72546f4f
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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