Tetrahydrofuran → HCID 86649314, Verbindung

HRID 1042294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042294
F[C:2]1[C:7]([C:8]2[N:16]=[CH:15][N:14]=[C:13]3[C:9]=2[N:10]=[CH:11][N:12]3[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[CH:6][CH:5]=[CH:4][N:3]=1.C[C:24]1[C:33]([NH2:34])=[C:32]2[C:27]([C:28](SC)=[N:29][CH:30]=[N:31]2)=[CH:26][CH:25]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1>CC(O)=O.O1CCOCC1>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[N:12]1[CH:11]=[N:10][C:9]2[C:13]1=[N:14][CH:15]=[N:16][C:8]=2[C:7]1[C:2]([C:30]2[N:29]=[CH:28][C:27]3[C:32](=[C:33]([NH2:34])[CH:24]=[CH:25][CH:26]=3)[N:31]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 444791786-(2-Fluoropyridin-3-YL)-9-(tetrahydro-2H-pyran-2-YL)-9H-purineHCID 596273877-Methyl-4-(methylthio)quinazolin-8-amine

Produkt 1

HCID 86649314HCID 86649314, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A 250 ml flask was charged with 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (2.92 g, 9.74 mmol) and 7-methyl-4-(methylthio)quinazolin-8-amine (2.00 g, 9.74 mmol) along with 20 ml of dioxane. 1.0 M LiHMDS in THF (29.2 ml, 29.2 mmol) was then added dropwise at RT. The reaction was stirred for 6 hrs and then treated with 5 ml of HOAc. The volatiles were removed under vacuum. The residue was dissolved in chloroform and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel eluting with a gradient of 20 to 60% EtOAc in hexanes to give 7-methyl-4-(methylthio)-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylquinazolin-8-amine as a yellow solid. MS Found: (ESI pos. ion) m/z 485 (M+H+).

Aufarbeitung

  1. customThe volatiles were removed under vacuum
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. custompurified by column chromatography on silica gel eluting with a gradient of 20 to 60% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-fccfe8f3a46145608d97893a85e11149
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557830B2

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