Sodium dichromate dihydrate → 4-(Methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde
Reaction equation
[CH3:1][NH:2][C:3]1[C:8]([CH2:9][OH:10])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1.O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C>[CH3:1][NH:2][C:3]1[C:8]([CH:9]=[O:10])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1Participants
Procedure
4-Methylamino-2-methylsulfanyl-5-pyrimidinemethanol (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.
Workup
- customAfter a total reaction time of 3.5 hours, the bright yellow solid was removed by filtration
- additionWater (30 mL) was added to the filtrate
- temperatureThe mixture was cooled in the refrigerator for 30 minutes
- customThe precipitate was collected
- dissolutiondissolved in ethyl acetate
- dry with materialthe solution was dried over MgSO4
- filtrationFiltration and concentration in vacuo
Sources & evidence
- ORD record
- ord-898c4a3b24714d1cb85564aa49dbacda
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05945422
Reaction notes
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