Ethanol → 4'-({4-[4-(2-Hydroxyethylidene)cyclohexyl]-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile

HRID 2048315Notes

Reaction equation

HRID 2048315 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].C(O)C.[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]2[C:25](=[O:48])[N:26]([CH:36]3[CH2:41][CH2:40][C:39](=[CH:42][C:43](OCC)=[O:44])[CH2:38][CH2:37]3)[C:27]3[N:28]([N:33]=[CH:34][N:35]=3)[C:29]=2[CH2:30][CH2:31][CH3:32])=[CH:19][CH:18]=1)#[N:10]>O1CCCC1>[OH:44][CH2:43][CH:42]=[C:39]1[CH2:40][CH2:41][CH:36]([N:26]2[C:25](=[O:48])[C:24]([CH2:23][C:20]3[CH:21]=[CH:22][C:17]([C:12]4[C:11]([C:9]#[N:10])=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:18][CH:19]=3)=[C:29]([CH2:30][CH2:31][CH3:32])[N:28]3[N:33]=[CH:34][N:35]=[C:27]23)[CH2:37][CH2:38]1

Participants

6

Reactant 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 86644029ethyl (4-{6-[(2'-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexylidene)acetate

Product 1

HCID 670092204'-({4-[4-(2-Hydroxyethylidene)cyclohexyl]-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrileYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of calcium chloride (1.6 g), sodium borohydride (1.1 g), tetrahydrofuran (40 mL) and ethanol (40 mL) was stirred at 0° C. for 1 hr. A solution (20 mL) of ethyl (4-{6-[(2′-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexylidene)acetate (1.9 g) in tetrahydrofuran was added to the reaction mixture, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was extracted with 1 N hydrochloric acid and ethyl acetate, and the obtained 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 (0.9 g, 49%).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. extractionThe reaction mixture was extracted with 1 N hydrochloric acid and ethyl acetate
  3. washthe obtained 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-6688993628d8401c8f7eafe075da2743
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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