Hydrochloric Acid → HCID 136026812, compound

HRID 1673686Notes

Reaction equation

HRID 1673686 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([CH2:11][O:12]C)[N:8]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:7](=[O:19])[C:6]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[NH:37][C:36](=[O:38])[O:35][N:34]=2)=[CH:23][CH:22]=1)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br.[OH-].[Na+].Cl>C(OCC)(=O)C.ClCCl>[CH2:1]([C:5]1[N:10]=[C:9]([CH2:11][OH:12])[N:8]([CH2:14][C:15]([CH3:17])([CH3:18])[CH3:16])[C:7](=[O:19])[C:6]=1[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[NH:37][C:36](=[O:38])[O:35][N:34]=2)=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 136026802HCID 136026802, compound

Product 1

HCID 136026812HCID 136026812, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-butyl-3-(2,2-dimethylpropyl)-2-(methoxymethyl)-5-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}pyrimidin-4(3H)-one (0.5 g), boron tribromide (1.0 M dichloromethane solution, 2.9 mL) and dichloromethane (20 mL) was stirred at room temperature for 3 hr, 0.5 M aqueous sodium hydroxide solution (10 mL) was added, and the mixture was further stirred for 1 hr. To the reaction mixture was added 1 M hydrochloric acid and adjusted to pH 5. Ethyl acetate was added, and the mixture was extracted. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.48 g, 98%).

Workup

  1. stirringthe mixture was further stirred for 1 hr
  2. extractionthe mixture was extracted
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4654d7b1c045400eafb32dc7bf532afb
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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