Tetrahydrofuran → HCID 178438591, compound

HRID 519665Notes

Reaction equation

HRID 519665 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)=[C:8]([CH2:25][CH2:26][CH3:27])[N:7]2[N:28]=[CH:29][N:30]=[C:6]2[N:5]1[CH:31]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]1.O1CCCC1.[Cl-].[NH4+]>CO>[OH:37][C@@H:34]1[CH2:35][CH2:36][C@H:31]([N:5]2[C:4](=[O:3])[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:13][CH:12]=3)=[C:8]([CH2:25][CH2:26][CH3:27])[N:7]3[N:28]=[CH:29][N:30]=[C:6]23)[CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride2×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-carbonitrile

Product 1

HCID 178438591HCID 178438591, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium tetrahydroborate (0.55 g) was dissolved in methanol (30 mL), a mixture 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 (5.9 g) and methanol (30 mL) was added dropwise at 0° C., and tetrahydrofuran (10 mL) was added. The mixture was stirred at room temperature for 1.5 hr, sodium tetrahydroborate (0.23 g) was added, and the mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The organic 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 (0.29 g, 13%).

Workup

  1. additionwas added dropwise at 0° C.
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. customThe solvent was evaporated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-38e8bb68908946978d3e4b2de590da4a
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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