Sodium Cyanide → 3-Cyanopropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate

HRID 870600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870600
[C-:1]#[N:2].[Na+].[CH2:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[NH:13][C:14]1[N:15]=[CH:16][C:17]2[CH2:22][N:21]([C:23]([O:25][CH2:26][CH2:27][CH2:28]Cl)=[O:24])[CH2:20][C:18]=2[N:19]=1>CN(C)C=O.ClCCl.O.[Cl-].[Li+]>[CH2:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[NH:13][C:14]1[N:15]=[CH:16][C:17]2[CH2:22][N:21]([C:23]([O:25][CH2:26][CH2:27][CH2:28][C:1]#[N:2])=[O:24])[CH2:20][C:18]=2[N:19]=1

Komponenten

7

Edukt 2

HCID 8929Sodium CyanideHCID 867265623-Chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate

Produkt 1

HCID 867265663-Cyanopropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylateAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 433294Lithium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Add sodium cyanide (0.230 g; 1.5 equiv; 4.69 mmoles) to a solution containing 3-chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (1.15 g; 1.0 equiv; 3.08 mmoles) in dimethylformamide (10 mL). Heat the reaction mixture to 100° C. for 3 hours, then cool to ambient temperature, dilute with dichloromethane, water, and 5% lithium chloride solution. Separate the layers and further extract the aqueous layer with dichloromethane and ethyl acetate. Dry the combined organic extracts over sodium sulfate, filter, and concentrate to provide 3-cyanopropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (0.98 g; 87%) as a brown solid: MS (m/z): 364(M+1).

Aufarbeitung

  1. temperaturecool to ambient temperature
  2. customSeparate the layers
  3. extractionfurther extract the aqueous layer with dichloromethane and ethyl acetate
  4. dry with materialDry the combined organic extracts over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-6e61a4b9f9f941f98265ba7396cab2c5
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969555B2

Notizen zur Reaktion

Wird geladen…