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

HRID 1174778

反応式

HRID 1174778 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 23665647Potassium tert-butoxide溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-eb1f3de82b724b838e7b8584d70893ab
出典データセット
uspto-grants-2010_11
特許番号
US07838525B2

関連ノート

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