Sodium Azide → HCID 89579596, Verbindung

HRID 928581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928581
Cl[C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][O:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:19][CH2:18]2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[N-:32]=[N+]=[N-].[Na+]>CN1C(=O)CCC1.C(Cl)Cl>[C:11]1([C:10]2[C:5]3[C:4]([N:17]4[CH2:22][CH2:21][CH:20]([CH2:23][O:24][CH2:25][CH2:26][N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)[CH2:19][CH2:18]4)=[N:3][C:2]([NH2:32])=[N:7][C:6]=3[S:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 89582576HCID 89582576, Verbindung

Produkt 1

HCID 89579596HCID 89579596, VerbindungAusbeute 20,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2-Chloro-5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine (0.4 g, 0.9 mmol) was dissolved in NMP (2 mL). Sodium azide (0.3 g, 4 mmol) was added and the reaction heated to 150° C. in the microwave for 30 minutes. The reaction mixture was diluted with DCM, washed with water, dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by basic prep HPLC (method 6) to afford 5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidin-2-amine as a brown gum (81 mg). LCMS RT=2.8 min. M+1=438.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated at reduced pressure
  4. customThe resulting residue was purified by basic prep HPLC (method 6)

Quellen und Nachweise

ORD-Eintrag
ord-10fb6cb615324e93bad9983ea209fc91
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290511B2

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