1-Naphthalenecarbonyl chloride → 3-Methyl-1-(2-methylpropyl)-6-(1-naphthalenylcarbonyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 567919

Reaktionsgleichung

Reaktionsgleichung von HRID 567919
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:18][N:19]1[C:24](=[O:25])[C:23]2[CH:26]=[CH:27][S:28][C:22]=2[N:21]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:20]1=[O:33]>ClCCCl>[CH3:18][N:19]1[C:24](=[O:25])[C:23]2[CH:26]=[C:27]([C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[O:12])[S:28][C:22]=2[N:21]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:20]1=[O:33]

Komponenten

5

Edukt 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 52825273-Methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 222579723-Methyl-1-(2-methylpropyl)-6-(1-naphthalenylcarbonyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

1-Naphthoyl chloride (1.25 ml) was added under nitrogen to a stirred slurry of aluminium chloride (1.1 g) in 1,2-dichloroethane (10 ml). A solution of 3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidin-2,4(1H,3H)-dione(2.0 g) in 1,2-dichloroethane (10 ml) was added dropwise and the resultant mixture was heated under reflux for 24 h and then allowed to cool to ambient temperature. The reaction mixture was quenched by the careful addition of water (2 ml) and was then concentrated in vacuo. The residue was dissolved in ethyl acetate and washed thrice with dilute hydrochloric acid, twice with saturated sodium hydrogen carbonate solution, and once with brine, then dried over magnesium sulfate and concentrated in vacuo. Purification by chromatography on silica gel eluting with toluene:ethyl acetate (9:1) gave the title compound (0.78 g).

Aufarbeitung

  1. temperatureunder reflux for 24 h
  2. customThe reaction mixture was quenched by the careful addition of water (2 ml)
  3. concentrationwas then concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed thrice with dilute hydrochloric acid
  6. dry with materialtwice with saturated sodium hydrogen carbonate solution, and once with brine, then dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography on silica gel eluting with toluene:ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-a28d44ddedc14d70ac1d73c482b9b87b
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180635B2

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