Reacción #3266

Ecuación de reacción

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

sodium dichromate-dihydrate

sodium dichromate-dihydrate

→

4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxaldehyde

Rendimiento 30.2%

Disolventes

acetic acid

acetic acid

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter 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
   TemperaturaThe mixture was cooled in the refrigerator for 30 minutes
4. 4
   OtroThe precipitate was collected
5. 5
   workup.DISSOLUTIONdissolved in ethyl acetate
6. 6
   Secadothe solution was dried over MgSO4
7. 7
   FiltraciónFiltration and concentration in vacuo

Procedimiento

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.

Fuente