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1,2-Dimethoxyethane → 2,2-dimethyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide

HRID 1780579
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HRID 1780579 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C(COC)OC.B([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])(O)O.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2]>[CH3:29][C:28]([CH3:31])([CH3:30])[C:27]([NH:26][C:20]1[CH:19]=[CH:24][C:23]([CH3:25])=[CH:22][C:21]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1)=[O:32]
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참가 물질

8

반응물 4

HCID 80711,2-DimethoxyethaneHCID 971134-Chloro-2-methylthiopyrimidineHCID 516892Sodium BicarbonateHCID 19045057N-(2-borono-4-methylphenyl)-2,2-dimethylpropanamide

생성물 1

HCID 190470412,2-dimethyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide수율 79.9%

시약·촉매·용매 3

HCID 84124
Bis(triphenylphosphine)palladium chloride
촉매
HCID 962Water용매
HCID 8857Ethyl Acetate용매2회

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온도
50 °C

실험 절차

A mixture of 16 g (0.1 mol) 4-chloro-2-(methylthio)pyrimidine, 0.150 g palladium bis(triphenylphosphine) dichloride, and 30 mL dimethoxyethane was stirred under nitrogen for 20 min, 25.8 g (0.11 mol) N-(2-borono-4-methyl phenyl)-2,2-dimethylpropanamide and a solution of 26 g sodium bicarbonate in 300 mL water was added, and the resulting mixture was heated to reflux for 5 h. After cooling to 50° C., 50 mL ethyl acetate was added and the reaction mixture was stirred until it reached room temperature. The reaction mixture was diluted with 300 mL ethyl acetate and washed successively with water and brine. The organic extracts were dried over magnesium sulfate, faltered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent to yield 25.2 g of the title compound as white crystals melting at 119°-20° C. 1H NMR (CDCl3): δ 1.28 (s,9H), 2.38 (s,3H), 2.60 (s,3H) 7.30-8.6 (5H), 11.3(s,1H,NH).

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 5 h
  3. stirringthe reaction mixture was stirred until it
  4. customreached room temperature
  5. washwashed successively with water and brine
  6. dry with materialThe organic extracts were dried over magnesium sulfate
  7. customevaporated to dryness
  8. customThe crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent

출처 및 근거

ORD 기록
ord-95c80df7d211486297ab7807c7f1de84
출처 데이터셋
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05631206

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