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

HRID 1843671
ノート
印刷プレビュー

反応式

HRID 1843671 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒
HCID 31275
1,4-Dioxane
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cdfcec428f69480b838df3a176e9d232
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946250B2

反応ノート

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