1,3,4-Thiadiazol-2-amine → 5,6-dimethyl-N2-(pyridin-2-ylmethyl)-N4-(1,3,4-thiadiazol-2-yl)pyrimidine-2,4-diamine

HRID 63182

Reaktionsgleichung

Reaktionsgleichung von HRID 63182
[CH:1]1([NH:6][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.[S:23]1C=[N:26][N:25]=[C:24]1N>>[CH3:13][C:12]1[C:7]([NH:6][C:1]2[S:23][CH:24]=[N:25][N:26]=2)=[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 199091,3,4-Thiadiazol-2-amineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Produkt 1

HCID 717389835,6-dimethyl-N2-(pyridin-2-ylmethyl)-N4-(1,3,4-thiadiazol-2-yl)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 1,3,4-thiadiazol-2-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 2.10 (s, 3H), 2.25 (s, 3H), 4.68 (d, J=2.0 Hz, 2H), 7.18-7.51 (m, 3H), 7.70 (t, J=7.8 Hz, 1H), 8.50 (s, 1H), 9.01 (s, 1H), 10.93 (bs, 1H); MS (ESI) m/z 314.1 (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-5277dbfa338241d8b46bf49c76b3d205
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447051B2

Verknüpfte Notizen

Wird geladen…