Water → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-amide

HRID 1958336

Reaktionsgleichung

Reaktionsgleichung von HRID 1958336
C[Al](C)C.[C:5]1([C:11]2[N:12]=[C:13]3[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]3[CH:20]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([O:23][C:24]([C:26]1[C:31]([NH:32][C:33]2[CH:34]=[N:35][CH:36]=[N:37][CH:38]=2)=[CH:30][CH:29]=[C:28]([CH:39]2[CH2:41][CH2:40]2)[N:27]=1)=O)C.O>O1CCOCC1.ClCCl.CO>[C:5]1([C:11]2[N:12]=[C:13]3[N:18]=[C:17]([NH:19][C:24]([C:26]4[C:31]([NH:32][C:33]5[CH:38]=[N:37][CH:36]=[N:35][CH:34]=5)=[CH:30][CH:29]=[C:28]([CH:39]5[CH2:40][CH2:41]5)[N:27]=4)=[O:23])[CH:16]=[CH:15][N:14]3[CH:20]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 16682925TrimethylaluminumHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amineHCID 58368056HCID 58368056, Verbindung

Produkt 1

HCID 534680246-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-amideAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Trimethylaluminum (2M solution in toluene, 0.26 ml) was added to a stirred suspension of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1, 111 mg) in dioxane (5 ml), and the mixture was stirred for 2 h at RT. 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester (50 mg) was then added in one portion, and the mixture was heated to 100° C. for 17 h. Upon cooling, water (0.5 ml) was added, followed by small amounts of methanol and dichloromethane to get an almost clear solution. Some Mg504 was added, the mixture was stirred for 15 min, and filtered. The filtrate was concentrated, and the title compound (44 mg, 56%) was isolated from the residue by column chromatography (silica gel, dichloromethane/methanol gradient), followed by trituration (methanol). MS (m/e)=449.2 [M+H+].

Aufarbeitung

  1. temperaturethe mixture was heated to 100° C. for 17 h
  2. temperatureUpon cooling
  3. customto get an almost clear solution
  4. additionSome Mg504 was added
  5. stirringthe mixture was stirred for 15 min
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-49790991f5054f039226de6d663fb53f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410117B2

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