Sodium Carbonate → 3-(3-bromo-5-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 731847노트

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HRID 731847 반응식
[Br:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.I[C:20]1[C:28]2[C:23](=[N:24][CH:25]=[N:26][C:27]=2[NH2:29])[N:22]([CH:30]([CH3:32])[CH3:31])[N:21]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[N:26][C:27]=3[NH2:29])[N:22]([CH:30]([CH3:32])[CH3:31])[N:21]=2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 159062002-(3-Bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 249053373-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

생성물 1

HCID 249051843-(3-bromo-5-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine수율 36%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

A solution of 2-(3-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (137 mg, 0.43 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (65 mg, 0.216 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80° C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA85 (28 mg, 36% yield). ESI-MS (M+H)+ m/z calcd 362.1, found 362.0.

후처리

  1. temperatureAfter cooling
  2. extractionthe reaction was extracted with saturated NaCl and CH2Cl2
  3. concentrationconcentrated in vacuo
  4. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

출처 및 근거

ORD 기록
ord-6eb7ee44ab5a434383babb7f5d438ce5
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585868B2

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