Reaktion #3266

Reaktionsgleichung

4-Methylamino-2-methylsulfanyl-5-pyrimidine-methanol

sodium dichromate-dihydrate

sodium dichromate-dihydrate

→

4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxaldehyde

Ausbeute 30.2%

Lösungsmittel

acetic acid

acetic acid

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter a total reaction time of 3.5 hours, the bright yellow solid was removed by filtration
2. 2
   workup.ADDITIONWater (30 mL) was added to the filtrate
3. 3
   TemperaturThe mixture was cooled in the refrigerator for 30 minutes
4. 4
   SonstigeThe precipitate was collected
5. 5
   workup.DISSOLUTIONdissolved in ethyl acetate
6. 6
   Trocknenthe solution was dried over MgSO4
7. 7
   FiltrationFiltration and concentration in vacuo

Vorschrift

4-Methylamino-2-methylsulfanyl-5-pyrimidine-methanol (2.40 g, 13.0 mmol) in 7 mL of acetic acid was added to a solution of sodium dichromate-dihydrate (1.30 g, 4.4 mmol) in 6 mL of acetic acid. After 2 hours at room temperature, additional sodium dichromate-dihydrate (0.3 g, 1.0 mmol) in 1 mL of acetic acid was added. After a total reaction time of 3.5 hours, the bright yellow solid was removed by filtration. Water (30 mL) was added to the filtrate, followed by aqueous ammonium hydroxide until basic (pH 9.0). The mixture was cooled in the refrigerator for 30 minutes. The precipitate was collected and dissolved in ethyl acetate, and the solution was dried over MgSO4. Filtration and concentration in vacuo gave 0.72 g (30%) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxaldehyde; mp 99°-101° C.

Quelle