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Chloroform → 5H-Thiazolo[3,2-a]pyrimidin-5-one, 6-bromo-7-methyl-

HRID 1583343
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1583343
[CH3:1][C:2]1[N:3]=[C:4]2[S:11][CH:10]=[CH:9][N:5]2[C:6](=[O:8])[CH:7]=1.C(OCC)(=O)CC(C)=O.[Br:21]N1C(=O)CCC1=O.C(Cl)(Cl)Cl>C1C=CC=CC=1>[Br:21][C:7]1[C:6](=[O:8])[N:5]2[CH:9]=[CH:10][S:11][C:4]2=[N:3][C:2]=1[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 8868Ethyl AcetoacetateHCID 67184N-bromobutanimideHCID 5970657-Methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

Produkt 1

HCID 14174045H-Thiazolo[3,2-a]pyrimidin-5-one, 6-bromo-7-methyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241
Benzene
Lösungsmittel

Versuchsvorschrift

7-methyl-5H-thiazolo[3,2-a]pyrimidine-5-one, m.p. 127°-129° C., (4 g), prepared according to Example 1 using ethyl acetoacetate, dissolved in benzene (100 ml) was reacted with N-bromo-succinimide (4.7 g) under stirring at room temperature for 1 hour. The precipitate was dissolved by adding chloroform and the solution was washed with water: evaporation in vacuo to dryness and crystallization of the residue from methanol gave 6-bromo-7-methyl-5H-thiazolo[3,2-a]pyrimidine-5-one, m.p. 233°-234° C. (5.1 g), which was reacted with 3-pyridine-carboxaldehyde (3.4 g) in methanol (190 ml) in the presence of sodium methoxide (2.2 g) under stirring at the reflux temperature for 2 hours. After cooling the precipitate was filtered and washed with water until neutral: crystallization from CH2Cl2 -methanol gave 5.18 g of 6-bromo-7-trans-[2-(3-pyridyl)-ethenyl]-5H-thiazolo[3,2-a]pyrimidine-5-one, m.p. 208°-209° C., NMR (CDCl3) δppm: 6.99 (d) (1H, C-2 proton), 7.33 (dd) (1H, C-5 pyridyl proton), 7.59 (d) (1H, β-ethenyl proton), 7.95 (d) (1H, α-ethenyl proton), 7.96 (d) (1H, C-3 proton), 7.98 (m) (1H, C-4 pyridyl proton), 8.58 (bd) (1H, C-6 pyridyl proton), 8.82 (bs) (1H, C-2 pyridyl proton); JHαHβ =16 Hz.

Aufarbeitung

  1. dissolutionThe precipitate was dissolved
  2. washthe solution was washed with water
  3. customevaporation in vacuo
  4. customto dryness and crystallization of the residue from methanol

Quellen und Nachweise

ORD-Eintrag
ord-985225907f9e42f9bf264d1811adb168
Quelldatensatz
uspto-grants-1985_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04551457

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