Reaktion #537067

Reaktionsgleichung

HCl

Methyl 4-methyl-3-oxopentanoate

Thiourea

K2CO3

→

6-isopropyl-2-mercaptopyrimidin-4-ol

Ausbeute 67.8%

Lösungsmittel

water

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter being cooled to room temperature
2. 2
   FiltrationThe white precipitate was collected by filtration
3. 3
   Waschenwashed with water and 1 N HCl

Vorschrift

Thiourea (1.0 g, 13 mmol) was dissolved in 1.6 mL of water at 70° C. Methyl 4-methyl-3-oxopentanoate (2.8 g, 20 mmol) was added and followed by K2CO3 (2.7 g, 19 mmol). The reaction was heated at 105° C. open to air for 1 hour to boil off any remaining methanol. After being cooled to room temperature, water (6.6 mL) was added and followed by 6 mL of concentrated HCl. The white precipitate was collected by filtration and washed with water and 1 N HCl to afford 6-isopropyl-2-mercaptopyrimidin-4-ol as a white solid (1.5 g, yield: 46%). 1H NMR (400 MHz, DMSO-d6): δ 12.34 (s, 1H), 12.19 (s, 1H), 5.67 (s, 1H), 2.66 (m, 1H), 1.13 (d, J=6.8 Hz, 6H). LCMS (ESI) m/z: 171.0 [M+H+].

Quelle