Реакция #3266

Уравнение реакции

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

sodium dichromate-dihydrate

sodium dichromate-dihydrate

→

4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxaldehyde

Выход 30.2%

Растворители

acetic acid

acetic acid

acetic acid

Условия реакции

Обработка

1. 1
   ДругоеAfter 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
   ТемператураThe mixture was cooled in the refrigerator for 30 minutes
4. 4
   ДругоеThe precipitate was collected
5. 5
   workup.DISSOLUTIONdissolved in ethyl acetate
6. 6
   Сушкаthe solution was dried over MgSO4
7. 7
   ФильтрацияFiltration and concentration in vacuo

Методика

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.

Источник