Triisopropyl borate → 2-(Dimethylamino)-4-methoxypyrimidin-5-ylboronic acid

HRID 2357660노트

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HRID 2357660 반응식
Br[C:2]1[C:3]([O:11][CH3:12])=[N:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.[B:13](OC(C)C)([O:18]C(C)C)[O:14]C(C)C.C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[CH3:9][N:8]([CH3:10])[C:5]1[N:4]=[C:3]([O:11][CH3:12])[C:2]([B:13]([OH:18])[OH:14])=[CH:7][N:6]=1

참가 물질

6

반응물 4

HCID 21531Triisopropyl borateHCID 25517Ammonium ChlorideHCID 6158295-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amineHCID 178418339Butyllithium

생성물 1

HCID 574164812-(Dimethylamino)-4-methoxypyrimidin-5-ylboronic acid수율 61.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

To a solution of 5-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amine (0.300 g, 1.29 mmol) and triisopropyl borate (0.416 mL, 1.81 mmol) in 7 mL of THF at −70° C. was added butyllithium (1.6 m in hexanes, 1.13 mL, 1.81 mmol) dropwise. The reaction stirred for 30 min at −70° C. and was allowed to warm up. At −20° C. ammonium chloride (sat.) was added. The mixture was extracted with ethyl acetate (3X). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give 250 mg of crude material, which was purified by column chromatography (5% MeOH in dichloromethane) to give 157 mg of 2-(dimethylamino)-4-methoxypyrimidin-5-ylboronic acid as a white solid. ES+=198.1 (M+H).

후처리

  1. temperatureto warm up
  2. extractionThe mixture was extracted with ethyl acetate (3X)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give 250 mg of crude material, which
  7. customwas purified by column chromatography (5% MeOH in dichloromethane)

출처 및 근거

ORD 기록
ord-0334a6bee2314bcfbb2b6d9dc9012b5c
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759337B2

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