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Potassium Carbonate → tert-Butyl [3-(2-{2-[(tert-butoxycarbonyl)amino]-5-[(2-chloro-5-methylpyrimidin-4-yl)amino]phenyl}ethyl)phenyl]carbamate

HRID 541901
ノート
印刷プレビュー

反応式

HRID 541901 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:6]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=2)[CH:7]=1.[Cl:32][C:33]1[N:38]=[C:37](Cl)[C:36]([CH3:40])=[CH:35][N:34]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:28]([O:27][C:25]([NH:24][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:35]2[C:36]([CH3:40])=[CH:37][N:38]=[C:33]([Cl:32])[N:34]=2)=[CH:7][C:6]=1[CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=1)=[O:26])([CH3:31])([CH3:30])[CH3:29]
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 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 57962696Carbamic acid,n-[3-[2-[5-amino-2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]ethyl]phenyl]-,1,1-dimethylethyl ester

生成物 1

HCID 57962029tert-Butyl [3-(2-{2-[(tert-butoxycarbonyl)amino]-5-[(2-chloro-5-methylpyrimidin-4-yl)amino]phenyl}ethyl)phenyl]carbamate収率 50.1%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a solution of tert-butyl [3-(2-{5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethyl)phenyl]carbamate (0.4 g, 0.9 mmol) (prepared in Example C52, step C) and 2,4-dichloro-5-methylpyrimidine (0.152 g, 0.936 mmol) in N,N-dimethylformamide (7 mL) was added potassium carbonate (0.662 g, 4.79 mmol). The resultant mixture was stirred overnight at rt overnight. 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 then dried (Na2SO4), filtered and concentrated to give the residue, which was purified by silica gel column chromatography to give the desired product (0.25 g, 39%). LCMS for C29H37ClN5O4 (M+H)+: m/z=554.2.

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
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the residue, which
  10. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9b3fd3d9314448c0a40c7f35ef6ce8aa
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…

このページの内容参加物実験手順後処理出典と根拠反応ノート