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Ammonium Chloride → 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-ethylpyrimidin-2-amine

HRID 45884
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HRID 45884 반응식
[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([C:10]2[C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=3)=[N:12][N:13]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:14]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2].[Cl-].[NH4+]>O1CCOCC1.O.[Zn]>[NH2:30][C:26]1[CH:25]=[C:24]([C:11]2[C:10]([C:8]3[CH:7]=[CH:6][N:5]=[C:4]([NH:3][CH2:1][CH3:2])[N:9]=3)=[CH:14][N:13]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[N:12]=2)[CH:29]=[CH:28][CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 67184314N-ethyl-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyrimidin-2-amine

생성물 1

HCID 671848314-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-ethylpyrimidin-2-amine수율 93.3%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매
HCID 31275
1,4-Dioxane
용매

실험 절차

391 mg (0.91 mmol) of N-ethyl-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyrimidin-2-amine were dissolved in a mixture of 20 ml of dioxane and 4 ml of water. 239 mg (3.64 mmol) of metallic zinc and 485 mg (9.1 mmol) of ammonium chloride were then added to the resulting solution. The reaction was carried out at 100° C. under stirring for 5 hours. The suspension was then filtered through a celite pad and the filtrate evaporated in vacuo. The residue was partitioned between dichloromethane and aqueous sodium hydrogenocarbonate and the organic layer dried over sodium sulphate and concentrated to give a crude purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 7/3), affording 340 mg (93%) of the title compound.

후처리

  1. customwas carried out at 100° C.
  2. filtrationThe suspension was then filtered through a celite pad
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was partitioned between dichloromethane and aqueous sodium hydrogenocarbonate
  5. dry with materialthe organic layer dried over sodium sulphate
  6. concentrationconcentrated
  7. customto give a crude
  8. custompurified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 7/3)

출처 및 근거

ORD 기록
ord-9ec0b154d1f64f3b860ac0fef64a2b2c
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541575B2

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