4-Methylmorpholine → Tert-butyl 2-[4-[3-[(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)amino]-2-methyl-3-oxopropyl]phenoxy]acetate

HRID 248055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248055
[CH3:1][C:2]([CH3:21])([O:4][C:5](=[O:20])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:19])[C:16]([OH:18])=O)=[CH:10][CH:9]=1)[CH3:3].CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:37]([N:40]1[C:47]([NH2:48])=[C:46]([NH2:49])[C:44](=[O:45])[N:43]([CH2:50][CH2:51][CH3:52])[C:41]1=[O:42])[CH2:38][CH3:39]>O1CCCC1.CN(C)C=O.C(OCC)C>[NH2:48][C:47]1[N:40]([CH2:37][CH2:38][CH3:39])[C:41](=[O:42])[N:43]([CH2:50][CH2:51][CH3:52])[C:44](=[O:45])[C:46]=1[NH:49][C:16](=[O:18])[CH:15]([CH3:19])[CH2:14][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][C:5]([O:4][C:2]([CH3:1])([CH3:3])[CH3:21])=[O:20])=[CH:13][CH:12]=1

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 197645314-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid

Produkt 1

HCID 45118932Tert-butyl 2-[4-[3-[(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)amino]-2-methyl-3-oxopropyl]phenoxy]acetateAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

Dissolve 4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid (1.07 g, 3.64 mmol) in tetrahydrofuran (15 mL) and treat with N-methylmorpholine (0.4 mL, 3.64 mmol). Cool to -20° C. and treat with isobutyl chloroformate (0.47 mL, 3.64 mmol). Stir for 30 minutes and add a solution of 1,3-dipropyl-5,6-diaminouracil (0.82 g, 3.64 mmol) in dimethylformamide (5 mL). Stir for 3 hours at -20° C., warm to room temperature and dilute with ethyl ether (200 mL). Separate the organic phase, wash with water (200 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography (5→10% methanol/chloroform then 5→10→20% isopropanol/hexane) to yield the title compound (1.66 g).

Aufarbeitung

  1. stirringStir for 3 hours at -20° C.
  2. temperaturewarm to room temperature
  3. customSeparate the organic phase
  4. washwash with water (200 mL)
  5. dry with materialdry (MgSO4)
  6. customEvaporate the solvent in vacuo
  7. custompurify by flash chromatography (5→10% methanol/chloroform

Quellen und Nachweise

ORD-Eintrag
ord-43cc7f1bbda14c34a7bc2d58eb985827
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208240

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