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

HRID 1366415노트

반응식

HRID 1366415 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cd8f4cf776b140569d2565e3d746efd1
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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