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Water → 1-[4-[4-(hydroxymethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea

HRID 2353691
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2353691
Cl[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C@@H:11]2[CH3:16])[N:3]=1.O.[O:18]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:41])[NH:25][C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)=[N:19]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.C(O)C>[OH:9][CH2:8][C:6]1[CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C@@H:11]2[CH3:16])[N:3]=[C:2]([C:29]2[CH:28]=[CH:27][C:26]([NH:25][C:24]([NH:23][C:20]3[CH:21]=[CH:22][O:18][N:19]=3)=[O:41])=[CH:31][CH:30]=2)[N:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 593799953-(1,2-Oxazol-3-yl)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaHCID 59380181[2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methanol

Produkt 1

HCID 593800101-[4-[4-(hydroxymethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea
Ausbeute 37,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

[2-Chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methanol (500 mg) was dissolved in an 18% DMF in a mixture of 7:3:2 DME:water:ethanol (10 mL). 3-(1,2-Oxazol-3-yl)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea (811 mg) and 2M aqueous sodium carbonate solution (4 mL) were then added to the solution and the resultant mixture degassed for 5 min. Dichlorobis(triphenylphosphine) palladium catalyst (73 mg) was added and the solution refluxed at 90° C. for 7 h under nitrogen atmosphere. The reaction was allowed to cool then neutralised with concentrated hydrochloric acid and loaded directly onto a SCX-2 column (50 g), the column was washed with methanol and the product eluted with 7N ammonia in methanol. The material was further purified by chromatography on silica, eluting with 5% methanol in DCM, to give the desired material (318 mg) as a white solid.

Aufarbeitung

  1. customthe resultant mixture degassed for 5 min
  2. additionDichlorobis(triphenylphosphine) palladium catalyst (73 mg) was added
  3. temperatureto cool
  4. washthe column was washed with methanol
  5. washthe product eluted with 7N ammonia in methanol
  6. customThe material was further purified by chromatography on silica
  7. washeluting with 5% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-8fa997a814404087ac61fd2ecfd7b6f6
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07750003B2

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