Sodium borohydride → 6-ethyl-3-[2-(4-fluorophenyl)-2-hydroxyethyl]-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

HRID 1889565Notes

Reaction equation

HRID 1889565 reaction equation
[CH2:1]([C:3]1[S:42][C:6]2[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]4[NH:40][C:39](=[O:41])[O:38][N:37]=4)=[CH:26][CH:25]=3)[C:8](=[O:22])[N:9]([CH2:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[O:14])[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[BH4-].[Na+]>C(Cl)(Cl)Cl.CO>[CH2:1]([C:3]1[S:42][C:6]2[N:7]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]4[NH:40][C:39](=[O:41])[O:38][N:37]=4)=[CH:28][CH:29]=3)[C:8](=[O:22])[N:9]([CH2:12][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[OH:14])[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1360523186-ethyl-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

Product 1

HCID 1360523096-ethyl-3-[2-(4-fluorophenyl)-2-hydroxyethyl]-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)-dioneYield 100%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of 6-ethyl-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 (0.5 g) in CHCl3-methanol (1:1, 30 mL) was added NaBH4 (0.039 g) at room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated, water was added and the mixture was adjusted to pH 5-6 with 1N hydrochloric acid and water, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the object compound (0.50 g, 100%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionextracted with ethyl acetate
  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-a36b4780958e4f0cb0aae4d6cd933a4c
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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