Morpholine → 5-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047162
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.O>[O:41]1[CH2:42][CH2:43][N:38]([C:2]2[CH:7]=[C:6]([N:8]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:15])([CH3:14])[CH3:16])[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[N:5]3[N:25]=[CH:26][C:27]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:4]3[N:3]=2)[CH2:39][CH2:40]1

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

Produkt 1

HCID 667335175-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amineAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (77.9 mg, 0.14 mmoL), morpholine (36.7 mg, 0.42 mmoL), NaHCO3 (53 mg, 0.63 mmoL) in NMP (3 mL) was heated at 130° C. overnight. The mixture was cooled to room temperature and diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation of solvent afforded the crude displacement compound. Purification by column chromatography afforded 5-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (70 mg, 82%). LCMS tR=2.72 Min (5 min run, UV254nm). Mass calculated for, M+ 606.3, observed LC/MS m/z 607.2 (M+H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. customEvaporation of solvent
  6. customafforded the crude displacement compound
  7. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-57361cf6508442c6bd37b8b45e0a1768
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591943B2

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