4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 68583496, 화합물

HRID 1989017

반응식

HRID 1989017 반응식
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:2].[CH2:15]([O:17][C:18]([C:20]1[C:21](Cl)=[N:22][C:23]([S:26][CH3:27])=[N:24][CH:25]=1)=[O:19])[CH3:16].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:15]([O:17][C:18]([C:20]1[C:21]([N:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])=[N:22][C:23]([S:26][CH3:27])=[N:24][CH:25]=1)=[O:19])[CH3:16]

참가 물질

5

반응물 3

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531DiisopropylethylamineHCID 243063Ethyl 3-(cyclohexylamino)propanoate

생성물 1

HCID 68583496HCID 68583496, 화합물수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-Cyclohexylamino-propionic acid ethyl ester (1.0 g, 5.0 mmol) and 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (1.17 g, 5.02 mmol) were combined in DCM (15 mL) and diisopropylethylamine (0.81 g, 6.3 mmol) was added. After 16 h, the solution was partitioned between water and DCM and the organic layer was dried (MgSO4) and concentrated. Chromatography (0-20% EtOAc/hexanes gradient) provided 1.63 g (84%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 8.39 (s, 1H) 5.30 (s, 1H), 4.30 (q, 2H, J=7.1 Hz), 4.14 (q, 1H, J=7.1 Hz), 3.76-3.80 (m, 2H), 2.65-2.69 (m, 2H), 2.49 (s, 3H), 1.81-1.84 (m, 2H), 1.34-1.40 (m, 7H), 1.12-1.27 (m, 7H).

후처리

  1. customthe solution was partitioned between water and DCM
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-885d4f060d6e4008ad5740447204df58
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642270B2

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