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

HRID 1780579
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1780579
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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

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

Produkt 1

HCID 190470412,2-dimethyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamideAusbeute 79,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 84124Bis(triphenylphosphine)palladium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-95c80df7d211486297ab7807c7f1de84
Quelldatensatz
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05631206

Notizen zur Reaktion

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