Imidazole → 3-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate

HRID 870596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870596
[H-].[Na+].[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[NH:12][C:13]1[N:14]=[CH:15][C:16]2[CH2:21][N:20]([C:22]([O:24][CH2:25][CH2:26][CH2:27]Cl)=[O:23])[CH2:19][C:17]=2[N:18]=1.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>CN(C)C=O.ClCCl>[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[NH:12][C:13]1[N:14]=[CH:15][C:16]2[CH2:21][N:20]([C:22]([O:24][CH2:25][CH2:26][CH2:27][N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)=[O:23])[CH2:19][C:17]=2[N:18]=1

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 867265623-Chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate

Produkt 1

HCID 867265613-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add sodium hydride (0.068 g; 2.25 equiv; 1.70 mmoles) to a solution of: 3-chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (0.283 g; 1.0 equiv; 0.76 mmoles), and 1H-imidazole (0.105 g; 2.0 equiv; 1.54 mmoles) in dimethylformamide (2.4 mL). Stir the reaction mixture for 16 hours, then dilute with dichloromethane and wash with water. Extract the aqueous layer with dichloromethane twice. Concentrate the combined organic extracts and then purify the crude product by column chromatography (0 to 10% methanol in dichloromethane) to afford of 3-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (0.0922 g; 30%) as a yellow solid: MS (m/z): 405(M+1).

Aufarbeitung

  1. washwash with water
  2. extractionExtract the aqueous layer with dichloromethane twice
  3. concentrationConcentrate the combined organic extracts
  4. custompurify the crude product by column chromatography (0 to 10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-3c12fbb077c646fbbf6c09a46dd60329
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969555B2

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