Tetrahydrofuran → 4'-{[3-[2-(4-fluorophenyl)-2-hydroxyethyl]-2,4-dioxo-6-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1889342Notes

Reaction equation

HRID 1889342 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:41])[CH2:9][N:10]2[C:15](=[O:16])[C:14]3[CH:17]=[C:18]([CH2:20][C:21]([F:24])([F:23])[F:22])[S:19][C:13]=3[N:12]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]4[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:28][CH:27]=3)[C:11]2=[O:40])=[CH:4][CH:3]=1.O1CCCC1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:41])[CH2:9][N:10]2[C:15](=[O:16])[C:14]3[CH:17]=[C:18]([CH2:20][C:21]([F:24])([F:23])[F:22])[S:19][C:13]=3[N:12]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]4[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:28][CH:27]=3)[C:11]2=[O:40])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 593518164'-{[3-[2-(4-fluorophenyl)-2-oxoethyl]-2,4-dioxo-6-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

Product 1

HCID 593515364'-{[3-[2-(4-fluorophenyl)-2-hydroxyethyl]-2,4-dioxo-6-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrileYield 45.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4′-{[3-[2-(4-fluorophenyl)-2-oxoethyl]-2,4-dioxo-6-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (0.9 g), tetrahydrofuran (20 mL) and methanol (20 mL) was added sodium borohydride (0.19 g), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was extracted with ethyl acetate and saturated aqueous ammonium chloride solution. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous sodium 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 oil (0.41 g, 45%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate and saturated aqueous ammonium chloride solution
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dcfce4c27dcc4fa99c4bf666161b564f
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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