Potassium Carbonate → 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-(tetrahydro-2H-pyran-2-yloxy) propyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63928

Reaktionsgleichung

Reaktionsgleichung von HRID 63928
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12](=[O:17])[N:11]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:10]=3[O:9][C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)=[CH:4][CH:3]=1.Br[CH2:36][CH2:37][CH2:38][O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC(=O)OCC.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:36][CH2:37][CH2:38][O:39][CH:40]4[CH2:45][CH2:44][CH2:43][CH2:42][O:41]4)[C:12](=[O:17])[N:11]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:10]=3[O:9][C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)=[CH:33][CH:34]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 1317372135-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 1317372145-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-(tetrahydro-2H-pyran-2-yloxy) propyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dioneAusbeute 151,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (25.88 mg, 0.01 mmol) in DMF (3 mL) was added 2-(3-bromopropoxy)tetrahydro-2H-pyran (11.2 mg, 0.05 mmol) and K2CO3 (6.9 mg, 0.05 mmol). The reaction was stirred at 60° C. for 2 h, cooled to RT, then was diluted with EA (12 mL) and water (4 mL). The organic layer was washed with brine (3 mL), dried over Na2SO4, and concentrated to a residue which was purified by chromatography PE/EA (5:1) to give 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1-((2-(trimethylsilyl)ethoxy)methyl) furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (10 mg, 30.7% yield) as an oil. LCMS: (M++Na) 681 and TR=2.289 min.

Aufarbeitung

  1. temperaturecooled to RT
  2. washThe organic layer was washed with brine (3 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a residue which
  5. customwas purified by chromatography PE/EA (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-a753e6a2f24b4fe8810ffb14d3560ef1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447114B2

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