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

HRID 1811920노트

반응식

HRID 1811920 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid용매HCID 516892Sodium Bicarbonate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-9fb71393c3fd464e99297cfc6c9edf8d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

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