4-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amine → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4-diamine

HRID 2386978Notizen

Reaktionsgleichung

Cl.Cl.[NH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=1.Cl[C:15]1[C:16]2[CH2:26][CH2:25][CH2:24][C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[C:17]=2[N:18]=[C:19]([NH2:21])[N:20]=1>COCCO.[OH-].[Na+]>[NH2:13][C:9]1[N:8]=[C:7]([NH:6][CH2:5][CH2:4][NH:3][C:15]2[C:16]3[CH2:26][CH2:25][CH2:24][C:23]4[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=4[C:17]=3[N:18]=[C:19]([NH2:21])[N:20]=2)[CH:12]=[CH:11][N:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

The product of Example 1E (155 mg, 0.686 mmol) and the product of Example 1C (140 mg, 0.571 mmol) were combined in 2-methoxyethanol (0.8 mL) and heated to 130° C. for three hours. The mixture was diluted with 1 N aqueous sodium hydroxide and extracted twice with methylene chloride. The organic layers were combined and dried over sodium sulfate and the mixture was absorbed on silica gel and purified using silica gel chromatography, eluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.62 (d, J=4.41 Hz, 1H) 7.50-7.56 (m, 1H) 7.26-7.34 (m, 2H) 7.19-7.26 (m, 1H) 6.67-6.75 (m, 1H) 5.85 (s, 2H) 5.70-5.81 (m, 4H) 3.37-3.52 (m, 4H) 2.44 (t, J=6.78 Hz, 2H) 2.08-2.18 (m, J=6.78, 6.78 Hz, 2H) 1.92-2.04 (m, 2H); MS (ESI+) m/z 363.9 (M+H)+.

Aufarbeitung

extractionextracted twice with methylene chloride
dry with materialdried over sodium sulfate
customthe mixture was absorbed on silica gel
custompurified
washeluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%)

Quellen und Nachweise

ORD-Eintrag: ord-58741ababeab4221b9dc1aef513a1670
Quelldatensatz: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08268846B2

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