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Water → 2-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide

HRID 1773625
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773625
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]([C:16]2[C:20]3[N:21]=[C:22](Cl)[N:23]=[CH:24][C:19]=3[S:18][CH:17]=2)=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C@@H:26]1([NH2:33])[CH2:31][CH2:30][CH2:29][CH2:28][C@@H:27]1[NH2:32].O.ClCCl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]([C:16]2[C:20]3[N:21]=[C:22]([NH:32][C@@H:27]4[CH2:28][CH2:29][CH2:30][CH2:31][C@@H:26]4[NH2:33])[N:23]=[CH:24][C:19]=3[S:18][CH:17]=2)=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 3429171,2-Diaminocyclohexane, cis-HCID 866613792-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide

Produkt 1

HCID 566465522-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 0.0885 g (0.233 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide in 2.33 mL of dioxane was added 0.168 mL (1.4 mmole) of cis-cyclohexane-1,2-diamine. The mixture was heated at 100 degrees for over night. Water and dichloromethane were added, separated. The aqueous layer was washed with dichloromethane twice. The 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 dichloromethane-0.7 N ammonia solution in methanol (gradient 100:0-90:10) gave 0.064 g of 2-(cis-2-amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide as a light yellow solid. MH+/Z=458.

Aufarbeitung

  1. temperatureThe mixture was heated at 100 degrees for over night
  2. customseparated
  3. washThe aqueous layer was washed with dichloromethane twice
  4. washThe organic layer was washed with aqueous sodium carbonate, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography
  9. washeluting with dichloromethane-0.7 N ammonia solution in methanol (gradient 100:0-90:10)

Quellen und Nachweise

ORD-Eintrag
ord-c41fd4dcc18c4526befbc949988f9254
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255110B2

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