4'-{[5-Oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile → HCID 67009650, compound

HRID 2048322Notes

Reaction equation

HRID 2048322 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[O:6]=[C:7]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)=[C:11]([CH2:28][CH2:29][CH3:30])[N:10]2[N:31]=[CH:32][N:33]=[C:9]2[N:8]1[CH:34]1CCC(=O)[CH2:36][CH2:35]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:4]=[C:3]1[CH2:36][CH2:35][CH:34]([N:8]2[C:7](=[O:6])[C:12]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:18][CH:19]=3)=[C:11]([CH2:28][CH2:29][CH3:30])[N:10]3[N:31]=[CH:32][N:33]=[C:9]23)[CH2:1][CH2:2]1

Participants

5

Reactant 2

HCID 670088534'-{[5-Oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrileHCID 178418339Butyllithium

Product 1

HCID 67009650HCID 67009650, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (15 mL) of methyltriphenylphosphonium bromide (1.2 g) in tetrahydrofuran was added n-butyllithium (1.6M hexane solution, 2 mL) at 0° C., and the mixture was stirred at the same temperature for 30 min. The reaction mixture was warmed to room temperature, and further stirred for 30 min. A solution (5 mL) of 4′-{[5-oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (1 g) in tetrahydrofuran was added, and the mixture was stirred at 70° C. for 3 hr. The insoluble material was filtered off, and the obtained filtrate was extracted with ethyl acetate and 1 N hydrochloric acid. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.8 g, 80%).

Workup

  1. stirringfurther stirred for 30 min
  2. stirringthe mixture was stirred at 70° C. for 3 hr
  3. filtrationThe insoluble material was filtered off
  4. extractionthe obtained filtrate was extracted with ethyl acetate and 1 N hydrochloric acid
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9af715e3df346a498b84ccd0f129b26
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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