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

HRID 75457ノート

反応式

HRID 75457 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-10012ad628a540849ce16f926bf6d2d0
出典データセット
uspto-grants-2014_09
特許番号
US08835429B2

反応ノート

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