Reaktion #664102

Reaktionsgleichung

3-(bromomethyl)pyridin-1-ium bromide

6-methyl-2-sulfanylpyrimidin-4-ol

triethylamine

→

6-methyl-2-[(pyridin-3-ylmethyl)sulfanyl]pyrimidin-4-ol

Ausbeute 39.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solid residue was removed by filtration
2. 2
   SonstigeThe filtrate was recovered
3. 3
   Sonstigeevaporated under reduced pressure
4. 4
   SonstigeThe solid material was removed by filtration
5. 5
   SonstigeThe filtrate was recovered
6. 6
   Sonstigeevaporated to dryness
7. 7
   FiltrationThe product was recovered by filtration
8. 8
   Waschenwashed with diethyl ether (2×20 mL)
9. 9
   Sonstigedried in vacuo

Vorschrift

A mixture 3-(bromomethyl)pyridin-1-ium bromide (550 mg, 2.5 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (285 mg, 2.0 mmol), and triethylamine (1.1 mL, 8.0 mmol) in absolute ethanol (10 mL) was stirred at room temperature overnight. The solid residue was removed by filtration. The filtrate was recovered and evaporated under reduced pressure. The solid product was suspended in acetone (50 mL). The solid material was removed by filtration. The filtrate was recovered and evaporated to dryness. The residue was suspended in water (50 mL). The product was recovered by filtration, washed with diethyl ether (2×20 mL), and dried in vacuo, affording 6-methyl-2-[(pyridin-3-ylmethyl)sulfanyl]pyrimidin-4-ol (181 mg, 39% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.19 (s, 3H), 4.36 (s, 2H), 6.00 (s (br), 1H), 7.32 (td, 1H, J=0.8 Hz, 7.8 Hz), 7.82 (dd, 1H, J=0.8 Hz, 7.8 Hz), 8.42 (dd, 1H, J=0.8 Hz, 4.7 Hz), 8.61 (d, 1H, J=1.8 Hz); M+ 234; HPLC purity: 98.1%.

Quelle