Ethyl Acetate → 4-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfanylpyrimidine

HRID 575630Notes

Reaction equation

HRID 575630 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:6](O)=[N:7][C:8]([S:11][CH3:12])=[N:9][CH:10]=1.O=P(Cl)(Cl)[Cl:21].CC(=O)OCC>[N+](C)(C)(C)C.[Cl-].CC#N>[Cl:21][C:6]1[C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:2]=2[F:1])=[CH:10][N:9]=[C:8]([S:11][CH3:12])[N:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 1785034745-(2,4-Difluorophenoxy)-2-methylsulfanylpyrimidin-4-ol

Product 1

HCID 1180215104-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfanylpyrimidineYield 70.6%

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

The title compound of step 1 (5.30 g, 19.63 mmol), POCl3 (18.06 g, 117.78 mmol), (Me)4NCl (3.23 g, 29.47 mmol) in dry CH3CN (60 mL) was refluxed for 12 h. The mixture was poured into ice-water (50 mL) and subjected to EA extractive work up. Concentration under vacuum gave impure title compound (4.0 g), which was carried on to the next step.

Workup

  1. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-2f82fdc61f9b4b55907d79248a37c441
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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