Sodium Carbonate → HCID 68726071, 화합물

HRID 1042260

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HRID 1042260 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 68726071HCID 68726071, 화합물수율 72%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

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]+

후처리

  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

출처 및 근거

ORD 기록
ord-2a0aae788b74406e95e301771b969413
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557830B2

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