Dimethylformamide → 4,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

HRID 2245024Notes

Reaction equation

HRID 2245024 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN([CH:9]=[O:10])C.O[C:12]1[NH:17][C:16]([S:18][CH3:19])=[N:15]C(=O)C=1.Cl[CH:22]=[C:23]([Cl:25])Cl>>[Cl:25][C:23]1[C:22]([CH:9]=[O:10])=[C:12]([Cl:3])[N:17]=[C:16]([S:18][CH3:19])[N:15]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6575TrichloroethyleneHCID 24813Phosphorus oxychlorideHCID 178503560HCID 178503560, compound

Product 1

HCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehydeYield 61%

Conditions

Temperature
80 °C

Procedure

To the solution of phosphorus oxychloride (65 mL, 0.70 mol) in trichloroethylene (46.5 mL) was added DMF (25 mL, 0.32 mol) slowly to keep the temperature between 5° C. to 10° C. The solution was then warmed up to room temperature before 6-hydroxy-2-(methylthio)-4(1H)-pyrimidinone (25 g, 0.16 mol) was added in portions. The resultant reaction mixture was heated at 80° C. overnight followed by concentration under vacuum. The resulting slurry like residue was poured into ice, stirred for 2 hours then filtered to afford the crude product. The crude product was further purified by recrystalization with hexane to afford 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde (21.3 g, 61%).

Workup

  1. custombetween 5° C. to 10° C
  2. additionwas added in portions
  3. customThe resultant reaction mixture
  4. concentrationfollowed by concentration under vacuum
  5. additionThe resulting slurry like residue was poured into ice
  6. filtrationthen filtered
  7. customto afford the crude product
  8. customThe crude product was further purified by recrystalization with hexane

Sources & evidence

ORD record
ord-925bb0174054490291d0a89555c9d813
Source dataset
uspto-grants-2010_03
Patent number
US07678801B2

Reaction notes

Loading…