4-Fluoro-2-methylaniline → N4-(4-fluoro-2-methylphenyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

HRID 63165

Reaktionsgleichung

Reaktionsgleichung von HRID 63165
C1(N[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:8]=2)CCCC1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([CH3:31])[CH:25]=1>>[F:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:8]=2)=[C:26]([CH3:31])[CH:25]=1

Komponenten

3

Edukt 2

HCID 679824-Fluoro-2-methylanilineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Produkt 1

HCID 71738862N4-(4-fluoro-2-methylphenyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Versuchsvorschrift

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 (4-fluoro-2-methylphenyl)amine 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, DMSO-d6) δ ppm 2.01 (s, 3H), 2.07 (s, 3H), 2.15 (s, 3H), 4.30 (bs, 2H), 6.68 (bs, 1H), 6.84-6.89 (m, 1H), 6.98-7.10 (m, 2H), 7.17 (t, J=7.3 Hz, 2H), 7.57-7.67 (m, 2H), 8.43 (d, J=4.2 Hz, 1H); MS (ESI) m/z 338.8 (M+1)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-82b90308baca407fa433ff877d36bdab
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447051B2

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