Triethylamine → 8-(2-Chloro-6-(chloromethyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane

HRID 75457

반응식

HRID 75457 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH2:9][Cl:10])[N:3]=1.Cl.[CH:12]12[NH:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][O:14][CH2:13]2.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([N:19]2[CH:12]3[CH2:18][CH2:17][CH:16]2[CH2:15][O:14][CH2:13]3)[CH:5]=[C:4]([CH2:9][Cl:10])[N:3]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 150017782,4-Dichloro-6-(chloromethyl)pyrimidineHCID 534011293-Oxa-8-azabicyclo(3.2.1)octane hydrochloride

생성물 1

HCID 866659078-(2-Chloro-6-(chloromethyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane수율 69%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A flask was charged with 2,4-dichloro-6-(chloromethyl)pyrimidine (prepared as reported in Bioorg. Med. Chem., 2002, 10, 525), 2.40 g, 12.15 mmol) in dichloromethane (30 mL) to give a yellow solution. 3-Oxa-8-azabicyclo[3.2.1]octane, HCl (33, 1.818 g, 12.15 mmol) and triethylamine (3.56 ml, 25.5 mmol) in dichloromethane (30 mL) were added slowly over 10 minutes, and the resulting solution was allowed to stir at room temperature for 16 hours, then concentrated. The crude product was added to a silica gel column and eluted with 0-40% ethyl acetate in hexanes to provide 8-(2-chloro-6-(chloromethyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane (2.30 g, 69%) as an off-white solid. HRMS; [M+H]+ Obs'd=274.0510, [M+H]+ Calc'd=274.0508

후처리

  1. customto give a yellow solution
  2. concentrationconcentrated
  3. additionThe crude product was added to a silica gel column
  4. washeluted with 0-40% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-10012ad628a540849ce16f926bf6d2d0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835429B2

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