Hydrochloric Acid → 4-(5-Methoxy-2-(6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

HRID 1811804

反応式

HRID 1811804 の反応式
O1CCOCC1.Cl.Cl[C:9]1[C:14]([C:15]2[N:20]=[C:19]([CH3:21])[N:18]=[C:17]([NH2:22])[N:16]=2)=[CH:13][C:12]([O:23][CH3:24])=[CH:11][N:10]=1.[NH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[N:30][CH:31]=1>>[CH3:24][O:23][C:12]1[CH:13]=[C:14]([C:15]2[N:20]=[C:19]([CH3:21])[N:18]=[C:17]([NH2:22])[N:16]=2)[C:9]([NH:25][C:26]2[CH:31]=[N:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[N:10][CH:11]=1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 811216-Methoxy-3-pyridinylamineHCID 866470484-(2-Chloro-5-methoxypyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

生成物 1

HCID 595483714-(5-Methoxy-2-(6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

反応条件

温度
140 °C

実験手順

1,4-dioxane (0.1 mL, 1.169 mmol) and 2 N HCl (0.219 mL, 0.437 mmol) was added to a mixture of 4-(2-chloro-5-methoxypyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (110 mg, 0.437 mmol) and 5-amino-2-methoxypyridine (Aldrich, St. Louis, Mo.) (81 mg, 0.656 mmol) in a microwave reaction vessel and the mixture was sealed and heated at 140° C. for 60 min in a Personal Chemistry microwave unit under microwave irradiation. After cooling, the resulting dark mixture was concentrated. Flash column chromatographic purification (short column, SiO2, pure DCM to 5% MeOH in DCM) provided the title compound mixed with starting material. This was washed with methanol several times and finally the solid was recrystallized from MeOH to give 4-(5-methoxy-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (21 mg, 0.062 mmol, 14.16% yield) as a yellow-green powder. LCMS (API-ES) m/z 340 (M+H)+; 1H NMR (400 MHz, d6-DMSO) δ 11.47 (s, 1H) 8.52 (d, J=2.74 Hz, 1H) 8.39 (d, J=3.33 Hz, 1H) 8.13-8.18 (m, 1H) 8.12 (d, J=3.13 Hz, 1H) 7.86 (br. s., 1H) 7.73 (br. s., 1H) 6.79 (d, J=8.80 Hz, 1H) 3.83 (s, 3H) 3.82 (s, 3H) 2.44 (s, 3H).

後処理

  1. customthe mixture was sealed
  2. temperatureAfter cooling
  3. concentrationthe resulting dark mixture was concentrated
  4. customFlash column chromatographic purification (short column, SiO2, pure DCM to 5% MeOH in DCM)

出典と根拠

ORDレコード
ord-caf65d02be214051be7767ab006bc541
出典データセット
uspto-grants-2013_01
特許番号
US08362241B2

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