Tetrahydrofuran → HCID 136052328, compound

HRID 1889482Notes

Reaction equation

HRID 1889482 reaction equation
[CH:1]1([C:4]2[S:43][C:7]3[N:8]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[C:37]5[NH:41][C:40](=[O:42])[O:39][N:38]=5)=[CH:27][CH:26]=4)[C:9](=[O:23])[N:10]([CH2:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=4)=[O:15])[C:11](=[O:12])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1.O1CCCC1.[BH4-].[Na+]>CO>[CH:1]1([C:4]2[S:43][C:7]3[N:8]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[C:37]5[NH:41][C:40](=[O:42])[O:39][N:38]=5)=[CH:27][CH:26]=4)[C:9](=[O:23])[N:10]([CH2:13][CH:14]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=4)[OH:15])[C:11](=[O:12])[C:6]=3[CH:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 136052282HCID 136052282, compound

Product 1

HCID 136052328HCID 136052328, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 6-cyclopropyl-3-[2-(4-fluorophenyl)-2-oxoethyl]-1-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.1 g), tetrahydrofuran (10 mL) and methanol (10 mL) was added sodium borohydride-(0.038 g), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was extracted with chloroform and saturated aqueous ammonium chloride solution. The chloroform layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as colorless crystals (0.074 g, 74%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with chloroform and saturated aqueous ammonium chloride solution
  3. washThe chloroform layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-b425478a075d4e20803ec77c9e2f6310
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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