Reaktion #91416

ord-dcaf64410d7f400ab111ee3a9bf91fc7

Reaktionsgleichung

Cc1nc(NCc2ccccn2)nc(NC2CCCC2)c1C
N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine
NC1CCC1
cyclobutanamine
CCC(CC)Nc1nc(NCc2ccccn2)nc(C)c1C
titled compound
CCC(CC)Nc1nc(NCc2ccccn2)nc(C)c1C
5,6-dimethyl-N4-(pentan-3-yl)-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe titled compound was synthesized
  2. 2
    SonstigeThe crude material was purified by column chromatography
  3. 3
    Wascheneluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1)
  4. 4
    Waschenthe final product was washed with diethyl ether

Vorschrift

The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using cyclobutanamine instead of cyclopentanamine. The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1), and then the final product was washed with diethyl ether to afford the titled compound as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 0.81 (t, J=7.3 Hz, 3H), 1.36-1.43 (m, 2H), 1.50-1.57 (m, 2H), 1.90 (s, 3H), 2.26 (s, 3H), 3.94-4.00 (m, 1H), 4.17 (bs, 1H), 4.72 (d, J=5.9 Hz, 2H), 5.72 (bs, 1H), 7.13 (t, J=7.5 Hz, 1H), 7.36 (d, J=7.3 Hz, 1H), 7.60 (t, J=7.5 Hz, 1H), 8.54 (d, J=4.8 Hz, 1H); MS (ESI) m/z 300.1 (M+1)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09447051B2uspto-grants-2016_09