Diisopropylethylamine → 4-[(9aS)-octahydropyrazino[2,1-c][1,4]oxazin-8-yl]-6-chloro-5-fluoro-2-methylpyrimidine

HRID 1366415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366415
Cl.Cl.[CH2:3]1[C@@H:8]2[CH2:9][NH:10][CH2:11][CH2:12][N:7]2[CH2:6][CH2:5][O:4]1.[Cl:13][C:14]1[C:19]([F:20])=[C:18](Cl)[N:17]=[C:16]([CH3:22])[N:15]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:13][C:14]1[N:15]=[C:16]([CH3:22])[N:17]=[C:18]([N:10]2[CH2:11][CH2:12][N:7]3[C@H:8]([CH2:3][O:4][CH2:5][CH2:6]3)[CH2:9]2)[C:19]=1[F:20]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidineHCID 66649934(S)-Octahydropyrazino[2,1-C][1,4]oxazine dihydrochloride

Produkt 1

HCID 866369294-[(9aS)-octahydropyrazino[2,1-c][1,4]oxazin-8-yl]-6-chloro-5-fluoro-2-methylpyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of (9aS)-octahydropyrazino[2,1-c][1,4]oxazine dihydrochloride (23.28 g, 108.2 mmol) in DCM (360 mL) was added 4,6-dichloro-5-fluoro-2-methylpyrimidine (19.59 g, 108.2 mmol) and N,N-diisopropylethylamine (68 mL, 390.4 mmol). The mixture was stirred for 2 h, and the resulting solution was diluted with DCM (100 mL) and washed with saturated aq. NaHCO3 (200 mL). The aqueous phase was extracted with a fresh portion of DCM (100 mL), and this organic phase was washed with saturated aq. NaHCO3 (50 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give (9aS)-8-(6-chloro-5-fluoro-2-methyl-4-pyrimidinyl)octahydropyrazino[2,1-c][1,4]oxazine as a light yellow oil that was used without further purification. LCMS: (M+H)+: 287.1.

Aufarbeitung

  1. washwashed with saturated aq. NaHCO3 (200 mL)
  2. extractionThe aqueous phase was extracted with a fresh portion of DCM (100 mL)
  3. washthis organic phase was washed with saturated aq. NaHCO3 (50 mL)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cd8f4cf776b140569d2565e3d746efd1
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

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