2-Iodoxybenzoic acid → HCID 178477520, Verbindung

HRID 63903

Reaktionsgleichung

Reaktionsgleichung von HRID 63903
[Br:1][C:2]1[S:23][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[C:9](=[O:10])[C:4]=2[C:3]=1[CH:24]=[O:25].I([C:29]1C=CC=C[C:30]=1C(O)=O)(=O)=O>CS(C)=O.O>[CH2:29]([SH:23]1[C:5]2[N:6]([CH3:22])[C:7](=[O:21])[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[C:9](=[O:10])[C:4]=2[C:3]([CH:24]=[O:25])=[C:2]1[Br:1])[CH3:30]

Komponenten

5

Edukt 2

HCID 1087942-Iodoxybenzoic acidHCID 1188631326-bromo-1-methyl-2,4-dioxo-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carbaldehyde2×

Produkt 1

HCID 178477520HCID 178477520, VerbindungAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 6-bromo-5-(bromomethyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (See Compound 2, Step 3, 800 mg, 1.61 mmol) in DMSO (10 mL) was added 2-iodoxybenzoic acid (541.7 mg, 1.93 mmol). The reaction was heated at 50° C. for 1.5 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 (20 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 ethyl 6-bromo-1-methyl-2,4-dioxo-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-1,2,3,4-tetrahydro thieno[2,3-d]pyrimidine-5-carbaldehyde (400 mg, 57.5% yield) as a white solid. LCMS: [MH+-THP] 347 and TR=1.665 min.

Aufarbeitung

  1. temperaturecooled to RT
  2. extractionextracted with EA (3×10 mL)
  3. washThe combined organic layers were washed with aq. NH4Cl (20 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-e134f5e72867454caa1bf920628872de
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447114B2

Verknüpfte Notizen

Wird geladen…