2-(3-Aminophenyl)ethan-1-ol → 4-[4-(1-Amino-1-methylethyl)phenyl]-5-chloro-N-[3-(2-hydroxyethyl)phenyl]pyrimidine-2-amine

HRID 1359450

Reaktionsgleichung

Reaktionsgleichung von HRID 1359450
C(OC([NH:8][C:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20](Cl)[N:19]=2)=[CH:14][CH:13]=1)([CH3:11])[CH3:10])=O)(C)(C)C.[NH2:26][C:27]1[CH:28]=[C:29]([CH2:33][CH2:34][OH:35])[CH:30]=[CH:31][CH:32]=1>>[NH2:8][C:9]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34][OH:35])[CH:28]=3)[N:19]=2)=[CH:16][CH:17]=1)([CH3:10])[CH3:11]

Komponenten

3

Edukt 2

HCID 149389872-(3-Aminophenyl)ethan-1-olHCID 181832304-[4-(1-Tert-butoxycarbonylamino-1-methylethyl)phenyl]-2,5-dichloropyrimidine

Produkt 1

HCID 99080254-[4-(1-Amino-1-methylethyl)phenyl]-5-chloro-N-[3-(2-hydroxyethyl)phenyl]pyrimidine-2-amineAusbeute 23,9 %

Versuchsvorschrift

The title compound was prepared from 4-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-2,5-dichloropyrimidine (1.50 g, 6.55 mmol) and 2-(3-aminophenyl)ethanol (942 mg, 6.87 mmol) following the method of Example 1. The crude product was purified by chromatography (Silica, 10% methanol in CH2Cl2) to give the title compound as a brown solid (600 mg) m.p. 184-185°. δH (d6DMSO) 9.77 (1H, s), 8.57 (1H, s), 7.79 (2H, d, J 8.4 Hz), 7.68 (2H, d, J 8.4 Hz), 7.61-7.58 (2H, m), 7.17 (1H, t, J 7.7 Hz), 6.82 (1H, d, J 7.4 Hz), 4.62 (1H, bs), 3.60 (2H, t, J 7.0 Hz), 2.68 (2H, t, J 7.1 Hz), 2.07 (2H, bs), 1.41 (6H, s); MS (ESI) 383 (MH+, 35Cl).

Aufarbeitung

  1. customThe crude product was purified by chromatography (Silica, 10% methanol in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-320179c34b854775b108570d348a9390
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06600037B1

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