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Dimethylformamide → 2-Chloro-N-(1-methyl-1h-benzimidazol-4-yl)-thieno[3,2-d]pyrimidine-7-carboxamide

HRID 1773618
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773618
[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.C(N(CC)C(C)C)(C)C.[CH3:23][N:24]([CH3:27])[CH:25]=O.C1CN(C(O[N:40]2N=[N:47][C:46]3[C:41]2=C[CH:43]=[CH:44][CH:45]=3)=[N+]2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.O>[CH3:23][N:24]1[C:27]2[CH:43]=[CH:44][CH:45]=[C:46]([NH:47][C:11]([C:8]3[C:6]4[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=4[S:10][CH:9]=3)=[O:13])[C:41]=2[N:40]=[CH:25]1
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Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 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 866896202-Chloro-N-(1-methyl-1h-benzimidazol-4-yl)-thieno[3,2-d]pyrimidine-7-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.050 g (0.233 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid, 0.0686 g (0.466 mmole) of 1-methyl-1H-benzol[d]imidazol-4-amine, 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 overnight. 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. Purification by silica gel chromatography, eluting with hexanes-ethyl acetate (gradient 50:50-0:100) gave 0.042 g of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (1-methyl-1H-benzoimidazol-4-yl)-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. customPurification by silica gel chromatography
  7. washeluting with hexanes-ethyl acetate (gradient 50:50-0:100)

Quellen und Nachweise

ORD-Eintrag
ord-89a4b8c1b8424214af09dede9380f797
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255110B2

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