Reaktion #484587

Reaktionsgleichung

4-(3-chloro-4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one

3-methyl-5-[3-(4-methyl-piperazin-1-yl)-3-oxo-propyl]-1H-pyrrole-2-carbaldehyde

→

title compound

Ausbeute 68.0%

4-(3-Chloro-4-fluoro-phenylamino)-5-{3-methyl-5-[3-(4-methyl-piperazin-1-yl)-3-oxo-propyl]-1H-pyrrol-2-ylmethylene}-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-one

Ausbeute 68.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled at room temperature for overnight
2. 2
   FiltrationThe precipitate was collected by vacuum filtration
3. 3
   Waschenwashed with ethanol (5×)
4. 4
   Sonstigedried

Vorschrift

A mixture of 4-(3-chloro-4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (70 mg, 0.25 mmol), 3-methyl-5-[3-(4-methyl-piperazin-1-yl)-3-oxo-propyl]-1H-pyrrole-2-carbaldehyde (79 mg, 0.3 mmol) and piperidine (3 drops) in ethanol (2 mL) was stirred in an oil bath at 65° C. for 2 hours. The reaction was cooled at room temperature for overnight. The precipitate was collected by vacuum filtration, washed with ethanol (5×) and dried to give 88.9 mg (68%) of the title compound. 1H NMR (360 MHz, DMSO-d6) δ 13.15 (s, 1H, NH), 11.55 (br s, 1H, NH), 9.08 (s, 1H), 8.27 (s, 1H), 7.69 (dd, J=2.5 & 6.9 Hz, 1H), 7.30-7.40 (m, 3H), 6.08 (d, J=2.23 Hz, 1H), 3.43 (m, 4H, 2×CH2), 2.89 (t, J=7.4 Hz, 2H, CH2), 2.68 (t, J=7.4 Hz, 2H, CH2), 2.24 (m, 4H, 2×CH2), 2.16 (s, 6H, 2×CH3). MS 524 [M++1].

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