홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Dimethylformamide → 3-{3-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-5-methyl-phenyl}-acrylonitrile

HRID 426168
노트
인쇄 미리보기

반응식

HRID 426168 반응식
Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1.Br[CH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]#[N:27])[CH:20]=[C:21]([CH3:23])[CH:22]=1.[H-].[Na+].[Cl-].[NH4+].[CH3:32][N:33](C=O)C>>[C:32]([CH:16]([C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1)[C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]#[N:27])[CH:20]=[C:21]([CH3:23])[CH:22]=1)#[N:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidineHCID 667054103-(3-Bromomethyl-5-methyl-phenyl)-acrylonitrile

생성물 1

HCID 667056503-{3-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-5-methyl-phenyl}-acrylonitrile
수율 16%

실험 절차

To a stirred mixture of 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (7.12 g, 32.88 mmol) and 3-(3-bromomethyl-5-methyl-phenyl)-acrylonitrile (5.7 g, 31.21 mmol) in anhydrous DMF (60 ml) at 0° C. (ice bath) under nitrogen atmosphere, was portionwise added 60% sodium hydride (2.76 g, 68.88 mmol). After stirring for 1 hr., the mixture was further stirred at room temperature for overnight. The mixture was then neutralized with aqueous saturated ammonium chloride solution and the crude product was extracted with ether and purified by silica gel column chromatography (eluent, EA: hexanes (from 1:4 to 1:2)) to afford 1.8 g (16%) of a pale yellow foam. 1H NMR (300 MHz, CDCl3) δ 1.12 (3H, d, J=6.9 Hz), 1.15 (3H, d, J=6.9 Hz), 2.37 (3H, s), 3.02 (1H, m), 4.01 (6H, s), 5.39 (1H, s), 5.87 (1H, d, J=16.5 Hz), 7.23 (1H, s), 7.25 (1H, s), 7.27 (1H, s), 7.33 (1H, d, J=16.5 Hz).

후처리

  1. stirring, the mixture was further stirred at room temperature for overnight
  2. extractionthe crude product was extracted with ether
  3. custompurified by silica gel column chromatography (eluent, EA: hexanes (from 1:4 to 1:2))

출처 및 근거

ORD 기록
ord-121e4c55bbf04429b888af7e32f8a2dc
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106064B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트