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

HRID 1780579
ノート
印刷プレビュー

反応式

HRID 1780579 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 84124
Bis(triphenylphosphine)palladium chloride
触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-95c80df7d211486297ab7807c7f1de84
出典データセット
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05631206

反応ノート

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