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Potassium Carbonate → tert-Butyl [2-((Z)-2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}vinyl)pyridin-4-yl]carbamate

HRID 541847
ノート
印刷プレビュー

反応式

HRID 541847 の反応式
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]\[C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[N:30]=[C:29](Cl)[C:28]([Cl:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:24][C:25]1[N:30]=[C:29]([NH:1][C:2]2[CH:3]=[C:4](/[CH:8]=[CH:9]\[C:10]3[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:13]=[CH:12][N:11]=3)[CH:5]=[CH:6][CH:7]=2)[C:28]([Cl:32])=[CH:27][N:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57962525tert-Butyl {2-[(Z)-2-(3-aminophenyl)vinyl]pyridin-4-yl}carbamate

生成物 1

HCID 57962220tert-Butyl [2-((Z)-2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}vinyl)pyridin-4-yl]carbamate収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

To a solution of tert-butyl {2-[(Z)-2-(3-aminophenyl)vinyl]pyridin-4-yl}carbamate (50.0 mg, 0.16 mmol) and 2,4,5-trichloropyrimidine (0.019 mL, 0.17 mmol) in N,N-dimethylformamide (0.50 mL) was added potassium carbonate (66.6 mg, 0.48 mmol). The resultant mixture was stirred for 16 hours at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine then dried (Na2SO4), filtered and concentrated to give the desired product as a light brown gum (66 mg, 90%). LCMS for C22H22Cl2N5O2 (M+H)+: m/z=458.0, 460.0.

後処理

  1. customThe reaction was quenched with water
  2. additionEtOAc was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialthen dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-b7fb1f81842141bdaa129de96808d842
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08871753B2

反応ノート

読み込み中…

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