Dimethylformamide → (E)-3-hydroxy-2-(2-(methylthio)pyrimidin-4-yl)acrylaldehyde

HRID 500705Notes

Reaction equation

CN([CH:4]=[O:5])C.[C:6](Cl)(=[O:10])[C:7](Cl)=O.C[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1>C(Cl)(Cl)Cl>[OH:5]/[CH:4]=[C:7](\[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)/[CH:6]=[O:10]

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of DMF (114.9 g, 1.57 mol) in CHCl3 (800 mL) was added dropwise oxalyl chloride (190.3 g, 1.50 mol) at 0° C. After the addition, the resulting mixture was warmed at 30° C. and stirred for 1 h. The mixture was allowed to cool to 0° C. and 4-methyl-2-(methylthio)pyrimidine (2) (100 g, 0.714 mol) was added to the mixture. The resulting mixture was warmed to 40° C. and stirred for 16 h. The reaction mixture was cooled to room temperature and filtered. The cake was washed with CHCl3 (150 mL×3) and dried in vacuum to give (E)-3-hydroxy-2-(2-(methylthio)pyrimidin-4-yl)acrylaldehyde (3) (342.0 g, 100%) as a yellow solid.

Workup

additionAfter the addition
temperatureto cool to 0° C.
temperatureThe resulting mixture was warmed to 40° C.
stirringstirred for 16 h
temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
washThe cake was washed with CHCl3 (150 mL×3)
customdried in vacuum

Sources & evidence

ORD record: ord-8fb7a98ec8ff47b0849d28537554deff
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772246B2

Reaction notes

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