2-Iodoxybenzoic acid → 1-methyl-5-(3-methylbutanoyl)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63898

Reaktionsgleichung

Reaktionsgleichung von HRID 63898
[OH:1][CH:2]([C:7]1[C:15]2[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][O:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[C:12](=[O:27])[N:11]([CH3:28])[C:10]=2[S:9][C:8]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:39])([F:38])[F:37])[CH:30]=1)[CH2:3][CH:4]([CH3:6])[CH3:5].I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.O>[CH3:28][N:11]1[C:10]2[S:9][C:8]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:37])([F:38])[F:39])[CH:30]=3)=[C:7]([C:2](=[O:1])[CH2:3][CH:4]([CH3:5])[CH3:6])[C:15]=2[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[C:12]1=[O:27]

Komponenten

5

Edukt 2

HCID 1087942-Iodoxybenzoic acidHCID 1188631145-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione2×

Produkt 1

HCID 1188631451-methyl-5-(3-methylbutanoyl)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 5-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (See Compound 22, Step 3, 50 mg, 0.088 mmol) in DMSO (5 mL) was added 2-iodoxybenzoic acid (49.1 mg, 0.176 mmol). The reaction was heated at 50° C. for 2 h, cooled to RT, diluted with water (20 mL) and extracted with EA (3×10 mL). The combined organic layers were washed with aq. NH4Cl (5 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (5:1 to 1:1) to give 1-methyl-5-(3-methylbutanoyl)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (30 mg, 60.2% yield) as an oil. LCMS: MH+ 569 and TR=2.186 min.

Aufarbeitung

  1. temperaturecooled to RT
  2. extractionextracted with EA (3×10 mL)
  3. washThe combined organic layers were washed with aq. NH4Cl (5 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a residue which
  6. customwas purified by chromatography
  7. washeluted with PE/EA (5:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-87d0a6eced544d36821d0f6c918c2bd5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447114B2

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