6-Bromopyrrolo[2,1-F][1,2,4]triazin-4-amine → 6-Methylpyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1094897

반응식

HRID 1094897 반응식
Br[C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH2:11].[CH3:12][Zn]C>O1CCOCC1>[CH3:12][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH2:11]

참가 물질

4

반응물 2

HCID 579552016-Bromopyrrolo[2,1-F][1,2,4]triazin-4-amineHCID 178477796HCID 178477796, 화합물

생성물 1

HCID 552886216-Methylpyrrolo[2,1-f][1,2,4]triazin-4-amine수율 79.8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

To a degassed solution of 6-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (Intermediate AAE) (316 mg, 1.48 mmol) and Bis(diphenylphosphino)ferrocenepalladium dichloride (30 mg, 0.037 mmol) in 1,4-dioxane (10 mL), was added dimethyl zinc (2.97 mL, 5.93 mmol, 2.0 M in toluene). The mixture was allowed to stir at 90° C. for 17 hr and then cooled to 0° C. The reaction was quenched with MeOH (1.0 mL) and partitioned between ethyl acetate (200 mL) and potassium phosphate dibasic pH 10 buffer (100 mL). The layers were separated and the organic phase was washed with brine, dried (Na2SO4), and concentrated to dryness. Trituration with Et2O afforded 175 mg (79%) of the desired product. 1H-NMR (DMSO-d6) δ 7.69 (s, 1H), 7.39 (s, 1H), 6.61 (s, 1H), 2.18 (s, 3H); MS [M+H]+=148.9; LCMS RT=1.16.

후처리

  1. temperaturecooled to 0° C
  2. customThe reaction was quenched with MeOH (1.0 mL)
  3. custompartitioned between ethyl acetate (200 mL) and potassium phosphate dibasic pH 10 buffer (100 mL)
  4. customThe layers were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-8917d9b986fb470e8d6cdd572f5cbb8a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133995B2

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