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

HRID 2357660ノート

反応式

HRID 2357660 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0334a6bee2314bcfbb2b6d9dc9012b5c
出典データセット
uspto-grants-2010_07
特許番号
US07759337B2

反応ノート

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