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

HRID 712232노트

반응식

HRID 712232 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f37c94cc85d34678b1799566141daa7f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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