4-Aminomethyltetrahydropyran → 6-Bromo-3-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine

HRID 1623379

반응식

HRID 1623379 반응식
Br[C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[O:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1>CC#N>[Br:8][C:6]1[N:7]=[C:2]([NH:17][CH2:16][CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)[C:3]([Cl:9])=[N:4][CH:5]=1

참가 물질

4

반응물 2

HCID 27732104-AminomethyltetrahydropyranHCID 533503583,5-Dibromo-2-chloropyrazine

생성물 1

HCID 729420696-Bromo-3-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine수율 61.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

To a scintillation vial containing 3,5-dibromo-2-chloropyrazine (1 g, 3.67 mmol) and TEA (1.024 ml, 7.34 mmol) was added MeCN (5 ml) and (tetrahydro-2H-pyran-4-yl)methanamine (0.557 g, 3.67 mmol). The homogenous reaction mixture was capped, and heated to 80° C. in a oil bath for 4 hr. The reaction mixture was concentrated to dryness, diluted with EtOAc and sequentially washed with sat NaHCO3, and sat NaCl. The organic layer was dried Na2SO4, filtered and concentrated. The crude was purified by column chromatography on silica gel (20% EtOAc/Hexane) to yield 6-bromo-3-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (688 mg, 2.244 mmol, 61.1% yield), yield), LCMS (m/z): 308.0 (MH+), retention time=0.94 min, and 6-bromo-5-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (55 mg, 0.179 mmol, 4.89% yield), LCMS (m/z): 308.0 (MH+), retention time=0.91 min.

후처리

  1. customThe homogenous reaction mixture was capped
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additiondiluted with EtOAc
  4. washsequentially washed with sat NaHCO3
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by column chromatography on silica gel (20% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-e940e6cdfc8e4cea8744fb038615e0ee
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778951B2

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