4,6-Dichloro-5-methylpyrimidine → 5-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

HRID 1174778

반응식

HRID 1174778 반응식
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[Cl:16][C:17]1[C:22]([CH3:23])=[C:21](Cl)[N:20]=[CH:19][N:18]=1>C1COCC1.CC(C)([O-])C.[K+]>[Cl:16][C:17]1[C:22]([CH3:23])=[C:21]([O:15][CH:12]2[CH2:11][CH2:10][N:9]([C:7]3[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=3)[CH2:14][CH2:13]2)[N:20]=[CH:19][N:18]=1

참가 물질

5

반응물 2

HCID 8188604,6-Dichloro-5-methylpyrimidineHCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

생성물 1

HCID 865973665-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole수율 72.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 23665647Potassium tert-butoxide용매

실험 절차

To a solution of 1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-ol (3.65 g, 17 mmol) and 4,6-dichloro-5-methyl pyrimidine (2.83 g, 17 mmol) in THF (70 mL), 1M potassium-t-butoxide in THF (16 mL, 16 mmol) was added dropwise. The mixture was stirred at room temperature for 10 min. The crude mixture was purified by column chromatography on silica gel with hexane/ethyl acetate (3:1 v/v) to provide 4-chloro-6-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-5-methyl-pyrimidine as a solid (4.15 g, 71%). Exact mass calculated for C15H20ClN5O2 337.13, found 338.2 (MH+).

후처리

  1. customThe crude mixture was purified by column chromatography on silica gel with hexane/ethyl acetate (3:1 v/v)

출처 및 근거

ORD 기록
ord-eb1f3de82b724b838e7b8584d70893ab
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838525B2

연결된 노트

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