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Dimethylformamide → Ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylate

HRID 606478
노트
인쇄 미리보기

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HRID 606478 반응식
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6][C:5]2=[O:17].C(OCC)(=O)C.[CH3:24][N:25](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[C:24]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6][C:5]2=[O:17])#[N:25]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 136014453Ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate

생성물 1

HCID 136054489Ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylate수율 68%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매
HCID 178418397
HCID 178418397, 화합물
촉매

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온도
80 °C

실험 절차

A suspension of ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate (2.00 g, 5.81 mmol), zinc cyanide (375 mg, 3.19 mmol) and tetrakis(triphenylphosphine)palladium (336 mg, 0.29 mmol) in DMF (10 mL) was stirred at 80° C. for 5 hr under argon atmosphere. After cooling to room temperature, ethyl acetate was added to the reaction mixture. The precipitated solid was collected by filtration, washed with ethyl acetate, diisopropyl ether and water, dried over diphosphorus pentaoxide under reduced pressure to give the title compound as a pale-yellow powder (965 mg, 68%).

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with ethyl acetate, diisopropyl ether and water
  4. dry with materialdried over diphosphorus pentaoxide under reduced pressure

출처 및 근거

ORD 기록
ord-9df02a159c364311a50b8e63885e558e
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915267B2

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