Cesium fluoride → Methyl 6-amino-2-(6-fluorobenzo[c][1,2,5]oxadiazol-5-yl)-5-methoxypyrimidine-4-carboxylate

HRID 1468973

反応式

HRID 1468973 の反応式
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14].[F:15][C:16]1[C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][C:19]2=[N:20][O:21][N:22]=[C:18]2[CH:17]=1.[F-].[Cs+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C.O>[NH2:1][C:2]1[N:7]=[C:6]([C:24]2[C:16]([F:15])=[CH:17][C:18]3=[N:22][O:21][N:20]=[C:19]3[CH:23]=2)[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14]

参加物

6

反応物 3

HCID 25953Cesium fluorideHCID 52270701Methyl 6-amino-2-chloro-5-methoxypyrimidine-4-carboxylateHCID 904038595-Fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]oxadiazole

生成物 1

HCID 90404596Methyl 6-amino-2-(6-fluorobenzo[c][1,2,5]oxadiazol-5-yl)-5-methoxypyrimidine-4-carboxylate収率 40.9%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 18373917Acetonitrile--water (1/1)溶媒

反応条件

温度
115 °C

実験手順

Methyl 6-amino-2-chloro-5-methoxypyrimidine-4-carboxylate (400 mg, 1.838 mmol), 5-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]oxadiazole (789 mg, 2.390 mmol), bis(triphenylphosphine)palladium(II) chloride (129 mg, 0.184 mmol), and cesium fluoride (558 mg, 3.68 mmol) were combined in 4 mL 1:1 ACN-water and heated at 115° C. for 30 min in a microwave reactor. The cooled reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with saturated NaCl, dried, and evaporated. The product was purified by flash chromatography (SiO2, eluting with 5-30% ethyl acetate in dichloromethane) to provide the title compound (240 mg, 39%).

後処理

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic phase was washed with saturated NaCl
  4. customdried
  5. customevaporated
  6. customThe product was purified by flash chromatography (SiO2, eluting with 5-30% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-095fa5622b374946892d12364e65bc40
出典データセット
uspto-grants-2015_04
特許番号
US09006250B2

関連ノート

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