4-Chloro-6-methyl-1,3,5-triazin-2-amine → 4-(2-Fluoro-5-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1811800

반응식

HRID 1811800 반응식
O1CCOCC1.[F:7][C:8]1[C:13](B(O)O)=[CH:12][C:11]([CH3:17])=[CH:10][N:9]=1.Cl[C:19]1[N:24]=[C:23]([CH3:25])[N:22]=[C:21]([NH2:26])[N:20]=1.C([O-])(=O)C.[K+]>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[F:7][C:8]1[C:13]([C:19]2[N:24]=[C:23]([CH3:25])[N:22]=[C:21]([NH2:26])[N:20]=2)=[CH:12][C:11]([CH3:17])=[CH:10][N:9]=1

참가 물질

6

반응물 4

HCID 305914-Chloro-6-methyl-1,3,5-triazin-2-amineHCID 312751,4-DioxaneHCID 517044Potassium AcetateHCID 447548582-Fluoro-5-methylpyridine-3-boronic acid

생성물 1

HCID 601547184-(2-Fluoro-5-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine수율 41%

시약·촉매·용매 1

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)촉매

반응 조건

온도
120 °C

실험 절차

1,4-Dioxane (3.00 mL, 8.5 mmol) was added to a mixture of bis(di-tert-butyl (4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Aldrich, St. Louis, Mo.) (0.27 g, 0.43 mmol), 2-fluoro-5-methylpyridin-3-ylboronic acid (1.6 g, 10 mmol), 4-chloro-6-methyl-1,3,5-triazin-2-amine (1.24 g, 8.5 mmol) and potassium acetate (2.5 g, 26 mmol) and the mixture was sealed and heated at 120° C. for 30 min under microwave irradiation. After cooling, the mixture was passed through a short plug of Celite® (diatomaceous earth). The filter cake was washed with DCM (3×20 mL). The combined organic phases were concentrated. Flash column chromatographic purification (short column, SiO2, pure DCM to 5% MeOH in DCM) provided 4-(2-fluoro-5-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.76, 41%) as a white solid which was used for the next step. LCMS (API-ES) m/z 220 (M+H)+.

후처리

  1. customthe mixture was sealed
  2. temperatureAfter cooling
  3. washThe filter cake was washed with DCM (3×20 mL)
  4. concentrationThe combined organic phases were concentrated
  5. customFlash column chromatographic purification (short column, SiO2, pure DCM to 5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-683714342ecf4efbb1ca438a249a50ec
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

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