O-Toluidine → 5,6-dimethyl-N4-(2-methylphenyl)-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

HRID 63157

Reaktionsgleichung

Reaktionsgleichung von HRID 63157
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.[NH2:23][C:24]1[C:25]([CH3:30])=[CH:26][CH:27]=[CH:28][CH:29]=1>>[CH3:13][C:12]1[C:7]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])=[N:8][C:9]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[N:10][C:11]=1[CH3:14]

Komponenten

3

Edukt 2

HCID 7242O-ToluidineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Produkt 1

HCID 717387505,6-dimethyl-N4-(2-methylphenyl)-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 o-toluidine 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 2.08 (s, 3H), 2.27 (s, 3H), 2.34 (s, 3H), 4.66 (d, J=3.2 Hz, 2H), 5.70 (bs, 1H), 6.14 (s, 1H), 7.01 (t, J=6.3 Hz, 1H), 7.13 (t, J=6.3 Hz, 2H), 7.18 (d, J=7.5 Hz, 1H), 7.24 (d, J=7.8 Hz, 1H), 7.58 (t, J=7.8 Hz, 1H), 7.84 (d, J=7.8 Hz, 1H), 8.54 (d, J=4.8 Hz, 1H); MS (ESI) m/z 320.7 (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-a067d9845f68431b83bcc710f6d953d0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447051B2

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