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

Dimethylbarbituric acid → HCID 67401263, 화합물

HRID 906641
노트
인쇄 미리보기

반응식

HRID 906641 반응식
[CH2:1]([N:4](CC=C)[CH2:5][C:6]1[S:7][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)[CH:2]=[CH2:3].CN1C(=O)CC(=O)N(C)C1=[O:33].CCN(C(C)C)C(C)C.[C:50](Cl)(=O)[C:51]1C=CC=[C:53]([O:57][CH3:58])[CH:52]=1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[CH2:21]([O:20][CH:17]1[CH2:18][CH2:19][N:14]([S:11]([C:8]2[S:7][C:6]([CH2:5][NH:4][C:1](=[O:33])[C:2]3[CH:3]=[CH:50][CH:51]=[CH:52][C:53]=3[O:57][CH3:58])=[CH:10][CH:9]=2)(=[O:12])=[O:13])[CH2:15][CH2:16]1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 69860Dimethylbarbituric acidHCID 74374m-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 67401054HCID 67401054, 화합물

생성물 1

HCID 67401263HCID 67401263, 화합물수율 37%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6344Dichloromethane용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of 326a (134 mg, 0.3 mmol), 1,3 Dimethylbarbituric acid (94 mg, 0.6 mmol) and Tetrakis(triphenylphosphine)palladium (12 mg, 0.01 mmol) were stirred under Argon in 3 mL CH2Cl2. The reaction was followed by HPLC until all starting material disappeared. The crude was evaporated to dryness and taken up in dry THF. To this solution was added DIEA (230 ul, 1.5 mmol) and 3-anisoylchloride 0.3 mmol). The reaction was stirred for 3 h, EtOAc was added and the organic layer was extracted with NaHCO3 sat, HCl (0.1N) and brine. The dry solution was evaporated and purified by flash chromatography on silica gel using cyclohexane/EtOAc 7:3 as eluent. 326 was obtained as an oil (54 mg, 37%): H1 NMR (CDCl3) δ 7.43-7.25 (m, 4H), 7.15-7.05 (m, 2H), 6.60 (m, 1H), 4.83 (d, J=6.0 Hz, 2H), 3.86 (s, 3H), 3.35 (d, J=6.6, 2H), 335-3.23 (m, 3H), 2.95 (m, 2H), 1.94 (m, 2H), 1.86 (m, 2H), 1.70-1.50 (m, 5H), 1.30-1.20 (m, 8H), 0.87 (t, J=6.8, 3H), M/Z APCI: 495.2 (M+1).

후처리

  1. customThe crude was evaporated to dryness
  2. extractionthe organic layer was extracted with NaHCO3
  3. customThe dry solution was evaporated
  4. custompurified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-619504d190014e88b882fa3e5b8944a8
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012995B1

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트