Hexane → Ethyl 1-[(5-bromopyrimidin-2-yl)methyl]-4-methyl-piperidine-4-carboxylate

HRID 712232ノート

反応式

HRID 712232 の反応式
Cl.[CH3:2][C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[Br:23][C:24]1[CH:25]=[N:26][C:27]([CH2:30]Br)=[N:28][CH:29]=1.CCCCCC>CCO>[Br:23][C:24]1[CH:25]=[N:26][C:27]([CH2:30][N:6]2[CH2:7][CH2:8][C:3]([CH3:2])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:5]2)=[N:28][CH:29]=1

参加物

6

反応物 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 19361804Ethyl 4-methylpiperidine-4-carboxylate hydrochlorideHCID 205577975-Bromo-2-(bromomethyl)pyrimidine

生成物 1

HCID 66977105Ethyl 1-[(5-bromopyrimidin-2-yl)methyl]-4-methyl-piperidine-4-carboxylate収率 73%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl 4-methylpiperidine-4-carboxylate hydrochloride (0.08 g, 0.48 mmol) in EtOH (5.0 mL) was added DIPEA (0.22 mL, 1.20 mmol) at rt and the mixture stirred at rt for 10 minutes followed by addition of 5-bromo-2-(bromomethyl)pyrimidine (0.10 g, 0.40 mmol). The reaction was heated up to 70° C. for 1 h. After completion of reaction (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 20% EtOAc:hexane to obtain the desired product as a yellow solid (0.10 g, 73% yield). 1H NMR (DMSO-d6): δ 1.09 (s, 3H), 1.13 (t, J=7.20 Hz, 3H), 1.45 (m, 2H), 2.00 (m, 2H), 3.12 (m, 2H), 3.32 (m, 2H), 3.62 (q, J=7.20 Hz, 2H), 4.08 (m, 2H) and 8.94 (s, 2H).

後処理

  1. temperatureThe reaction was heated up to 70° C. for 1 h
  2. customAfter completion of reaction (by TLC), solvent
  3. customwas evaporated
  4. customthe crude residue purified over 100-200 M silica-gel

出典と根拠

ORDレコード
ord-f37c94cc85d34678b1799566141daa7f
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

読み込み中…