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Sodium hydride → 2-amino-8-(2,6-dichlorobenzyl)-6-(2,6-dichlorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3230
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인쇄 미리보기

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HRID 3230 반응식
[H-].[Na+].[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11](=[O:22])[NH:10][C:8]=2[N:9]=1.Br[CH2:24][C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32]>CN(C)C=O>[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=3[Cl:20])[C:11](=[O:22])[N:10]([CH2:24][C:25]3[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:32])[C:8]=2[N:9]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 104949152-Amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol

생성물 1

HCID 116124122-amino-8-(2,6-dichlorobenzyl)-6-(2,6-dichlorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one수율 35.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

To a suspension of NaH (60% in mineral oil, 36 mg) in 8 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (208 mg, 0.68 mmol). The mixture was heated at 70° C. for 10 minutes and then at 50° C. for 30 minutes, resulting in a clear solution. α-Bromo-2,6-dichlorotoluene (215 mg, 0.90 mmol) was added, and the reaction mixture was heated at 50° C. for 25 minutes, then poured onto ice water. The resulting precipitate was removed by filtration and washed with water. The solid was purified by flash chromatography, eluting with 1:1 hexane:ethyl acetate then dried in vacuo to provide 112 mg (35%) of 2-amino-8-(2,6-dichlorobenzyl)-6-(2,6-dichlorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one; mp 274°-276° C.

후처리

  1. customresulting in a clear solution
  2. temperaturethe reaction mixture was heated at 50° C. for 25 minutes
  3. additionpoured onto ice water
  4. customThe resulting precipitate was removed by filtration
  5. washwashed with water
  6. customThe solid was purified by flash chromatography
  7. washeluting with 1:1 hexane
  8. dry with materialethyl acetate then dried in vacuo

출처 및 근거

ORD 기록
ord-eccbafead2a446cdb38d33e16b8e1e3f
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05733914

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