Sodium Carbonate → 1,1-Dimethylethyl 3-(2-amino-5-pyrimidinyl)benzoate

HRID 500170

反応式

HRID 500170 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.[C:15]([O:19][C:20]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>O.C(O)C.C1(C)C=CC=CC=1.CCOC(C)=O.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>[NH2:14][C:11]1[N:10]=[CH:9][C:8]([C:26]2[CH:27]=[C:22]([CH:23]=[CH:24][CH:25]=2)[C:20]([O:19][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:21])=[CH:13][N:12]=1

参加物

9

反応物 3

HCID 10340Sodium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 2773299(3-((Tert-butoxy)carbonyl)phenyl)boronic acid

生成物 1

HCID 672241101,1-Dimethylethyl 3-(2-amino-5-pyrimidinyl)benzoate収率 73.5%

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

Sodium carbonate (0.636 g, 6.0 mmol) in water (2.0 mL) was added to a mixture of 5-bromopyrimidin-2-amine (0.348 g, 2.0 mmol), [3-(tert-butoxycarbonyl)phenyl]boronic acid (0.533 g, 2.4 mmol) and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) in ethanol (3.0 mL) and toluene (3.0 mL). The resulting mixture was heated at 120° C. for 3 h. The mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was treated with methanol. The precipitate was filtered and dried to give the product (399 mg, 73.5%). 272.1.

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was treated with methanol
  6. filtrationThe precipitate was filtered
  7. customdried

出典と根拠

ORDレコード
ord-3aa96d66fb73468896e7114210d6fdc7
出典データセット
uspto-grants-2010_08
特許番号
US07767675B2

関連ノート

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