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N,N-Diethylaniline → 4-Chloro-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine

HRID 1926901
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HRID 1926901 반응식
C(N(CC)C1C=CC=CC=1)C.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:28]3[C:27](=O)[NH:26][CH:25]=[N:24][C:23]=3[O:22][CH:21]=2)=[CH:16][CH:15]=1.P(Cl)(Cl)([Cl:32])=O>C1(C)C=CC=CC=1>[Cl:32][C:27]1[C:28]2[C:20]([C:17]3[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=3)=[CH:21][O:22][C:23]=2[N:24]=[CH:25][N:26]=1
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참가 물질

5

반응물 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychloride2회HCID 580169685-(4-Methoxyphenyl)furo[2,3-d]pyrimidin-4(3H)-one

생성물 1

HCID 580168144-Chloro-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

Add 14.5 ml (13.6 g, 90.8 mmol) N,N-diethylaniline to a suspension of 10.0 g (41.3 mmol) 5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4(3H)-one in 250 ml toluene and heat to 100° C. At this temperature, add 4.2 ml (7.0 g, 45.4 mmol) phosphoryl chloride dropwise, and stir the reaction mixture for 15 h at 100° C. Then add a further 1.2 ml (2.0 g, 13 mmol) phosphoryl chloride and stir the reaction mixture again for 22 h at 100° C. After cooling to room temperature, quickly wash the reaction solution with, successively, 250 ml ice water, twice with 250 ml cold 20% sodium hydroxide solution each time, again with 250 ml ice water, 250 ml satd. sodium chloride solution, 1 N hydrochloric acid and 250 ml ice water. Dry the organic phase over sodium sulphate, filter and concentrate by vacuum evaporation. 6.3 g (59% of theor.) of the title compound is obtained.

후처리

  1. stirringstir the reaction mixture again for 22 h at 100° C
  2. temperatureAfter cooling to room temperature
  3. washquickly wash the reaction solution with, successively, 250 ml ice water
  4. dry with materialDry the organic phase over sodium sulphate
  5. filtrationfilter
  6. concentrationconcentrate by vacuum evaporation

출처 및 근거

ORD 기록
ord-b72774a25f7145fabf6e6be97d61cd41
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183246B2

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