Potassium Carbonate → 8-Chloro-5-pyrimidin-4-yl-1-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene

HRID 1243598ノート

反応式

HRID 1243598 の反応式
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:35]1[CH:40]=[CH:39][N:38]=[CH:37][N:36]=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][N:12]([C:35]4[CH:40]=[CH:39][N:38]=[CH:37][N:36]=4)[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:18][CH2:19]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 6428344-ChloropyrimidineHCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

生成物 1

HCID 219256128-Chloro-5-pyrimidin-4-yl-1-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene収率 13.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

A mixture of the amine from example 4 (500 mg, 1.3 mmol), potassium carbonate (480 mg, 3.5 mmol) and 4-chloropyrimidine (300 mg, 2.6 mmol) was stirred at 95° C. for 18 hours. The cooled reaction mixture was diluted with ethyl acetate and the solution was washed with brine (5×), then dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol (100:0 to 95:5) as eluant, and the product was triturated with diethyl ether to afford the title compound (80 mg).

後処理

  1. customThe cooled reaction mixture
  2. washthe solution was washed with brine (5×)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel
  6. customthe product was triturated with diethyl ether

出典と根拠

ORDレコード
ord-7b09d6d4234f4bd5ac43cda0bd91d6b3
出典データセット
uspto-grants-2006_10
特許番号
US07119088B2

反応ノート

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