Dimethylformamide → 5-{2-Amino-6-[3-(3-tert-butoxycarbonylaminopropoxy)phenylsulfanyl]pyrimidin-4-yl}-2-methoxy-4-methylbenzoic acid methyl ester

HRID 1811755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811755
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)[N:13]=[C:12]([NH2:24])[N:11]=2)[C:7]([CH3:25])=[CH:6][C:5]=1[O:26][CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[C:40]([O:44][C:45](=[O:51])[NH:46][CH2:47][CH2:48][CH2:49]Br)([CH3:43])([CH3:42])[CH3:41]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:49][CH2:48][CH2:47][NH:46][C:45]([O:44][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:51])[CH:18]=3)[N:13]=[C:12]([NH2:24])[N:11]=2)[C:7]([CH3:25])=[CH:6][C:5]=1[O:26][CH3:27]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 592246605-[2-Amino-6-(3-hydroxyphenylsulfanyl)pyrimidin-4-yl]-2-methoxy-4-methylbenzoic acid methyl ester

Produkt 1

HCID 592246785-{2-Amino-6-[3-(3-tert-butoxycarbonylaminopropoxy)phenylsulfanyl]pyrimidin-4-yl}-2-methoxy-4-methylbenzoic acid methyl esterAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-[2-Amino-6-(3-hydroxyphenylsulfanyl)pyrimidin-4-yl]-2-methoxy-4-methylbenzoic acid methyl ester (80 mg, 0.2 mmol) obtained in Step 1 above, cesium carbonate (124 mg, 0.38 mmol), and N,N-dimethylformamide (1.0 ml) were added to a reaction vessel. Then 3-bromopropylcarbamic acid tert-butyl ester (100 mg, 0.42 mmol) was added to the mixture. The mixture was stirred at room temperature for 37 hours. The reaction solution was diluted with ethyl acetate (100 ml), and sequentially washed twice with a saturated aqueous ammonium chloride solution (50 ml), twice with water (50 ml), and with a saturated aqueous sodium chloride solution (50 ml). The washed ethyl acetate solution was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate) to yield 5-{2-amino-6-[3-(3-tert-butoxycarbonylaminopropoxy)phenylsulfanyl]pyrimidin-4-yl}-2-methoxy-4-methylbenzoic acid methyl ester (103 mg).

Aufarbeitung

  1. washsequentially washed twice with a saturated aqueous ammonium chloride solution (50 ml), twice with water (50 ml)
  2. dry with materialThe washed ethyl acetate solution was dried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-16c64ec6019b425a959ce11d1e79315d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362236B2

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