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3,4,5-Trimethoxyaniline → 2-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide

HRID 1773624
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773624
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]([OH:13])=O)[C:6]=2[N:7]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[NH2:19].C(N(CC)C(C)C)(C)C.C1CN(C(ON2N=NC3C2=CC=CC=3)=[N+]2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.O.CN(C)C=O>[CH3:26][O:25][C:21]1[CH:20]=[C:18]([NH:19][C:11]([C:8]2[C:6]3[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=3[S:10][CH:9]=2)=[O:13])[CH:17]=[C:16]([O:15][CH3:14])[C:22]=1[O:23][CH3:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 322853,4,5-TrimethoxyanilineHCID 81531DiisopropylethylamineHCID 13685355O-(Benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium HexafluorophosphateHCID 580563052-Chlorothieno[3,2-D]pyrimidine-7-carboxylic acid

Produkt 1

HCID 866613792-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.050 g (0.233 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid, 0.0854 g (0.466 mmole) of 3,4,5-trimethoxyaniline, 0.122 mL (0.699 mmole) of N,N-diisopropylethylamine and 1.55 mL of dimethylformamide was added 0.111 g (0.256 mmole) of O-(benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate. The mixture was stirred at room temperature for 2 hours. Water and dichloromethane were added. The aqueous layer was washed three times with dichloromethane. The combined organic layer was washed with aqueous sodium carbonate, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dried in high vacuum to give 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide as a yellow solid

Aufarbeitung

  1. washThe aqueous layer was washed three times with dichloromethane
  2. washThe combined organic layer was washed with aqueous sodium carbonate, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was dried in high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-24bd8791008c4730bbb7c2c35c369197
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255110B2

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