Trifluoromethanesulfonic acid → 4-(3-(6-Methoxypyridin-3-ylamino)pyridin-4-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1811920ノート

反応式

HRID 1811920 の反応式
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][C:16]=3[NH:21][C:22]3[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[N:12]=[C:11]([CH3:30])[N:10]=2)=CC=1.FC(F)(F)S(O)(=O)=O>C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>[CH3:29][O:28][C:25]1[N:24]=[CH:23][C:22]([NH:21][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:15]=2[C:13]2[N:12]=[C:11]([CH3:30])[N:10]=[C:9]([NH2:8])[N:14]=2)=[CH:27][CH:26]=1

参加物

5

反応物 2

HCID 62406Trifluoromethanesulfonic acidHCID 66600265N,N-bis(4-methoxybenzyl)-4-(3-(6-methoxypyridin-3-ylamino)pyridin-4-yl)-6-methyl-1,3,5-triazin-2-amine

生成物 1

HCID 595482504-(3-(6-Methoxypyridin-3-ylamino)pyridin-4-yl)-6-methyl-1,3,5-triazin-2-amine収率 81%

試薬・触媒・溶媒 2

HCID 6422Trifluoroacetic acid溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A glass microwave reaction vessel was charged with N,N-bis(4-methoxybenzyl)-4-(3-(6-methoxypyridin-3-ylamino)pyridin-4-yl)-6-methyl-1,3,5-triazin-2-amine (7 mg, 0.013 mmol) and trifluoromethane sulfonic acid (3.38 μL, 0.038 mmol) in TFA (0.1 mL). The reaction mixture was stirred and heated in an oil bath at room temperature for 2 h. The reaction mixture was diluted with saturated NaHCO3 (5 mL) and extracted with EtOAc (2×20 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow solid. The crude product was purified by silica gel chromatography eluting with EtOAc to give 4-(3-(6-methoxypyridin-3-ylamino)pyridin-4-yl)-6-methyl-1,3,5-triazin-2-amine (3.2 mg, 10.35 μmol, 81% yield). 1H NMR (300 MHz, CDCl3) δ 10.38 (s, 1H); 8.38 (s, 1H); 8.24 (d, J=5.12 Hz, 1H); 8.13 (s, 1H); 8.07 (d, J=4.97 Hz, 1H); 7.58 (dd, J=8.77, 2.05 Hz, 1H); 6.81 (d, J=8.77 Hz, 1H); 5.41 (s, 2H); 3.96 (s, 3H); 2.54 (s, 3H). m/z (ESI, +ve ion) 310.0 (M+H)+.

後処理

  1. customA glass microwave reaction vessel
  2. extractionextracted with EtOAc (2×20 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (5 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material as a light-yellow solid
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with EtOAc

出典と根拠

ORDレコード
ord-9fb71393c3fd464e99297cfc6c9edf8d
出典データセット
uspto-grants-2013_01
特許番号
US08362241B2

反応ノート

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