Hydrochloric Acid → 2-Methylsulfanylpyrimidine-4-carbaldehyde
Reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([S:10][CH3:11])[N:5]=1.Cl.C(=O)(O)[O-].[Na+]>>[CH3:11][S:10][C:6]1[N:5]=[C:4]([CH:3]=[O:2])[CH:9]=[CH:8][N:7]=1Participants
4
Conditions
- Temperature
- 60 °C
Procedure
4-(dimethoxymethyl)-2-(methylthio)pyrimidine (3) (53.7 g, 268 mmol) was added carefully to 1.2 N aqueous HCl (300 mL, 268 mmol, 1.0 equiv.) and stirred at 60° C. for 3 hours. The reaction mixture was then cooled to room temperature and neutralized by the slow addition of solid sodium bicarbonate. The crude mixture was extracted with diethyl ether (3×150 mL) and the combined organic layer was concentrated under reduced pressure to afford 2-(methylthio)pyrimidine-4-carbaldehyde (4) as a yellow solid (14.2 g, 41.5 g theoretical, 34%). LC-MS m/z 155 (M+1). Reference: WO 2006/009734 A1, pg 67.
Workup
- temperatureThe reaction mixture was then cooled to room temperature
- extractionThe crude mixture was extracted with diethyl ether (3×150 mL)
- concentrationthe combined organic layer was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-964e6ae41ac3433da776cca4c2e77ec5
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09157077B2
Reaction notes
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