Water → (2,5-Dichloro-pyrimidin-4-yl)-(3-morpholin-4-yl-phenyl)-amine

HRID 1040901

Reaktionsgleichung

Reaktionsgleichung von HRID 1040901
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[O:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=2)[NH2:25])[CH2:18][CH2:17]1.O>O1CCCC1.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:22]([N:19]3[CH2:20][CH2:21][O:16][CH2:17][CH2:18]3)[CH:23]=2)[C:5]([Cl:9])=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 8477683-(Morpholin-4-yl)aniline

Produkt 1

HCID 86633892(2,5-Dichloro-pyrimidin-4-yl)-(3-morpholin-4-yl-phenyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,4,5-Trichloropyrimidine (0.960 g, 5.2 mmol) was dissolved in tetrahydrofuran (20 mL). Potassium carbonate (1.20 g, 8.70 mmol) was added, followed by 3-morpholinoaniline (0.875 g, 4.90 mmol). After stirring overnight, water (30 mL) and dichloromethane (30 mL) were added, the phases separated and the aqueous layer extracted once with dichloromethane (30 mL). The combined organic fractions were dried over sodium sulfate, concentrated onto silica gel and chromatographed (120 g SiO2, 0-50% EA:Hex). (2,5-Dichloro-pyrimidin-4-yl)-(3-morpholin-4-yl-phenyl)-amine was isolated as an off-white solid (1.16 g, 73%). m.p.=142-145° C.; LCMS (m/e) 325 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 8.20 (s, 1H), 7.38 (s, 1H), 7.28 (m, 1H), 7.21 (s, 1H), 7.01 (d, 1H, J=7.8 Hz), 6.75 (d, 1H, J=8.4 Hz), 3.88 (t, 4H, J=4.8 Hz), 3.21 (t, 4H, J=4.8 Hz).

Aufarbeitung

  1. customthe phases separated
  2. extractionthe aqueous layer extracted once with dichloromethane (30 mL)
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. concentrationconcentrated onto silica gel
  5. customchromatographed (120 g SiO2, 0-50% EA:Hex)

Quellen und Nachweise

ORD-Eintrag
ord-f5fff7ba29584c36a30311c4ce750b5e
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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