1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → 1-(5-Bromothien-2-ylmethyl)-5-chloropyrimidin-2-one

HRID 434655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 434655
C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[NH:22][CH:23]=1.[Br:25][C:26]1[S:30][C:29]([CH2:31]O)=[CH:28][CH:27]=1>CN(C)C=O>[Br:25][C:26]1[S:30][C:29]([CH2:31][N:20]2[CH:19]=[C:18]([Cl:17])[CH:23]=[N:22][C:21]2=[O:24])=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 11435467(5-Bromothiophen-2-yl)methanol

Produkt 1

HCID 204917611-(5-Bromothien-2-ylmethyl)-5-chloropyrimidin-2-oneAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

N,N-Dimethylformamide dineopentyl acetal (2.25 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (653 mg) and 5-bromo-2-hydroxymethylthiophene (1.351 g) in dry N,N-dimethylformamide (12.5 ml) under nitrogen and then the mixture was heated at 40° C. After 2 h the temperature was increased to 80° C. After 4 h the reaction mixture was evaporated to dryness and the residue triturated with diethyl ether. The solid was collected and crystallised from acetone to give off white crystals of the title pyrimidinone (691 mg), m.p. 217°-220° C., λmax (EtOH) 243.5 nm (ε 13,810), 336 nm (ε 1,190).

Aufarbeitung

  1. temperatureAfter 2 h the temperature was increased to 80° C
  2. customAfter 4 h the reaction mixture was evaporated to dryness
  3. customthe residue triturated with diethyl ether
  4. customThe solid was collected
  5. customcrystallised from acetone

Quellen und Nachweise

ORD-Eintrag
ord-8983776e7a9a42ca87ea3ed0d4d526b3
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04399140

Notizen zur Reaktion

Wird geladen…