Hydrochloric Acid → 6-ethyl-3-[2-(methoxyimino)-3,3-dimethylbutyl]-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 1889527Notes

Reaction equation

HRID 1889527 reaction equation
[CH3:1][C:2]([CH3:39])([CH3:38])[C:3](=O)[CH2:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[C:13]([CH2:15][CH3:16])[S:14][C:8]=2[N:7]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[NH:34][C:33](=[O:35])[O:32][N:31]=3)=[CH:20][CH:19]=2)[C:6]1=[O:36].Cl.[NH2:41][O:42][CH3:43].N1C=CC=CC=1.Cl>O.C(OCC)(=O)C.C(O)C>[CH2:15]([C:13]1[S:14][C:8]2[N:7]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:34][C:33](=[O:35])[O:32][N:31]=4)=[CH:20][CH:19]=3)[C:6](=[O:36])[N:5]([CH2:4][C:3](=[N:41][O:42][CH3:43])[C:2]([CH3:38])([CH3:1])[CH3:39])[C:10](=[O:11])[C:9]=2[CH:12]=1)[CH3:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 136052251HCID 136052251, compound

Product 1

HCID 1363483416-ethyl-3-[2-(methoxyimino)-3,3-dimethylbutyl]-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 36.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(3,3-dimethyl-2-oxobutyl)-6-ethyl-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 (0.20 g), (aminooxy)methane hydrochloride (0.15 g), pyridine (2 mL) and ethanol (2 mL) was stirred at 100° C. for 16 hr. To the reaction mixture were added ethyl acetate and water, and the mixture was adjusted to pH 4 with 1N hydrochloric acid. The organic layer was washed with saturated brine, and dried over anhydrous magnesium 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 amorphous solid (0.077 g, 36%).

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fcec00dc676e4a12ab43ac9b236b937d
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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