Nitrogen → 5-isopropyl-N-methylpyridin-2-amine

HRID 594816

반응식

HRID 594816 반응식
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)([CH3:3])[CH3:2].N#N.[Li][CH2:14]CCC.IC>C1COCC1.O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH3:14])=[N:8][CH:9]=1)([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 947NitrogenHCID 6328Methyl iodideHCID 179858055-(Propan-2-yl)pyridin-2-amineHCID 178418339Butyllithium

생성물 1

HCID 208238975-isopropyl-N-methylpyridin-2-amine수율 36.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of 5-isopropyl-pyridin-2-ylamine (0.5 g, 3.67 mmol) in dry THF was purged with N2 and cooled to −78° C. n-BuLi (1.62 mL, 4.04 mmol) was added dropwise. The reaction was stirred at 0° C. for 0.5 h, and then iodomethane (0.25 mL, 4.04 mmol) was added dropwise. The resulting mixture was stirred overnight while warming to r.t. Water (20 mL) was added, and the mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated, and purified by silica gel chromatography (10% to 30% EtOAc in PE) to give 200 mg (36%) of the title compound as a brown oil. [M+H] Calc'd for C9H14N2, 151. Found, 151.

후처리

  1. additionwas added dropwise
  2. stirringThe resulting mixture was stirred overnight
  3. temperaturewhile warming to r.t
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (10% to 30% EtOAc in PE)

출처 및 근거

ORD 기록
ord-7b88ec5d0e78410095cff08470740bd3
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242968B2

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