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4-(2-(Diethylamino)ethoxy)aniline → 3-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1858247
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HRID 1858247 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([CH:23]2[CH2:28][CH2:27][CH2:26][CH:25]=[CH:24]2)[C:10]1=[O:29].[CH2:30]([N:32]([CH2:43][CH3:44])[CH2:33][CH2:34][O:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1)[CH3:31]>ClCCl.CO.C(O)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:40][C:39]3[CH:38]=[CH:37][C:36]([O:35][CH2:34][CH2:33][N:32]([CH2:43][CH3:44])[CH2:30][CH3:31])=[CH:42][CH:41]=3)=[N:15][CH:16]=2)[N:11]([CH:23]2[CH2:28][CH2:27][CH2:26][CH:25]=[CH:24]2)[C:10]1=[O:29]
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참가 물질

4

반응물 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 221250623-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

생성물 1

HCID 221250143-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one수율 22%

시약·촉매·용매 1

HCID 18914200Dichloromethane methanol acetic acid water
용매

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온도
180 °C

실험 절차

A mixture of 70 mg (0.15 mmol) of 3-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one and 150 mg (0.7 mmol) of 4-[2-(diethylamino)ethoxy]aniline was heated at 180° C. for 35 minutes and then cooled. The residue was subjected to column chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution. Product-containing fractions were combined and evaporated and the residue was evaporated with toluene. The residue was then dissolved in 30 ml of dichloromethane, washed twice with 20 ml of saturated aqueous sodium bicarbonate solution each time, dried over magnesium sulfate, filtered and evaporated to give 5 mg (22%) of 3-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as an orange colored gum. [Mass spectrum (ESI) MH+ =581].

후처리

  1. temperaturecooled
  2. washfor the elution
  3. customevaporated
  4. customthe residue was evaporated with toluene
  5. dissolutionThe residue was then dissolved in 30 ml of dichloromethane
  6. washwashed twice with 20 ml of saturated aqueous sodium bicarbonate solution each time
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-d776d5854da742dd8ab5797cbba688da
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06150373

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