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

HRID 500170

반응식

HRID 500170 반응식
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

참가 물질

9

반응물 3

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

생성물 1

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

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3aa96d66fb73468896e7114210d6fdc7
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767675B2

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