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

HRID 1366415ノート

反応式

HRID 1366415 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cd8f4cf776b140569d2565e3d746efd1
出典データセット
uspto-grants-2011_02
特許番号
US07893056B2

反応ノート

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