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Ammonium Hydroxide → 6-(3-(6-Methoxypyridin-3-ylamino)pyrazin-2-yl)-2-methylpyrimidin-4-amine

HRID 1621511
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HRID 1621511 반응식
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[CH:21]=[C:20](S(C)=O)[N:19]=[C:18]([CH3:25])[N:17]=3)=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.[OH-].[NH4+:27]>O1CCOCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[N:17]=[C:18]([CH3:25])[N:19]=[C:20]([NH2:27])[CH:21]=3)=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1
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참가 물질

4

반응물 2

HCID 14923Ammonium HydroxideHCID 66600383N-(6-Methoxypyridin-3-YL)-3-(2-methyl-6-(methylsulfinyl)pyrimidin-4-YL)pyrazin-2-amine

생성물 1

HCID 595484026-(3-(6-Methoxypyridin-3-ylamino)pyrazin-2-yl)-2-methylpyrimidin-4-amine수율 83%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A glass microwave reaction vessel was charged with N-(6-methoxypyridin-3-yl)-3-(2-methyl-6-(methylsulfinyl)pyrimidin-4-yl)pyrazin-2-amine (11.40 mg, 0.032 mmol) (crude product from the last step) and ammonium hydroxide, 28.0-30.0% (0.5 mL, 12.84 mmol) in dioxane (1 mL). The reaction mixture was stirred and heated in an oil bath at 100° C. for 2 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 80% EtOAc/hexanes to give 6-(3-(6-methoxypyridin-3-ylamino)pyrazin-2-yl)-2-methylpyrimidin-4-amine (8.2 mg, 0.027 mmol, 83% yield). 1H NMR (300 MHz, CDCl3) δ 12.46 (s, 1H); 8.42 (s, 1H); 8.15 (s, 1H); 8.10 (dd, J=8.77, 2.48 Hz, 1H); 7.98 (d, J=1.32 Hz, 1H); 7.47 (s, 1H); 6.78 (d, J=8.62 Hz, 1H); 4.95 (s, 2H); 3.95 (s, 3H); 2.64 (s, 3H). m/z (ESI, +ve ion) 310.1 (M+H)+.

후처리

  1. customA glass microwave reaction vessel
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 80% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-4719201727874014a5d8d47a645465e6
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772480B2

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