Sodium Carbonate → HCID 68726071、化合物

HRID 1042260

反応式

HRID 1042260 の反応式
[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9](B(O)O)=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:27]1[C:28]2[CH:35]=[CH:34][NH:33][C:29]=2[N:30]=[CH:31][N:32]=1>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([C:27]2[C:28]3[CH:35]=[CH:34][NH:33][C:29]=3[N:30]=[CH:31][N:32]=2)=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 2735950(2,4-Di-tert-butoxypyrimidin-5-yl)boronic acidHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

生成物 1

HCID 68726071HCID 68726071、化合物収率 72%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

2,4-Di-tert-butoxypyrimidin-5-ylboronic acid (17.5 g, 65.4 mmol), tetrakis(triphenylphosphine) palladium(0) (7.6 g, 6.54 mmol) and sodium carbonate (20.8 g, 196 mmol) were added to a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (10 g, 65.4 mmol) in DME (400 mL) and water (150 mL). With vigorous stirring, the mixture was heated to 80° C. for 24 h. The reaction mixture was cooled to RT and poured into water (100 mL). The mixture was extracted with EtOAc (100 mL) twice. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude product. This was purified by flash chromatography to give 4-(2,4-di-tert-butoxypyrimidin-5-yl)-7H-pyrrolo[2,3-d]pyrimidine (16.0 g, 72%) as a yellow solid. MS (APCI, pos. ion) m/z: 342.1 [M+H]+

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionThe mixture was extracted with EtOAc (100 mL) twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThis was purified by flash chromatography

出典と根拠

ORDレコード
ord-2a0aae788b74406e95e301771b969413
出典データセット
uspto-grants-2013_10
特許番号
US08557830B2

関連ノート

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