Phosphorus oxychloride → HCID 22648011, compound

HRID 394092Notes

Reaction equation

HRID 394092 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([S:15][CH3:16])[N:12]=[C:11](O)[C:10]=1[CH3:18].O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:11]1[C:10]([CH3:18])=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[N:14]=[C:13]([S:15][CH3:16])[N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178503547HCID 178503547, compound

Product 1

HCID 22648011HCID 22648011, compound

Procedure

A solution of 5.9 g of 6-(2,4-difluorophenyl)-5-methyl-2-(methylthio)pyrimidin-4-ol in 25 mL of POCl3 was heated to reflux and stirred at this temperature for 5 h. All but ca. 5 mL of POCl3 was removed by vacuum distillation, and the residue was quenched by pouring into 200 mL of ice-water, neutralizing with Na2CO3 and extracting with 3×100 mL of EtOAc. The combined organics were washed with 100 mL of brine, dried, and concentrated. The residue was purified by flash chromatography on a Biotage 40M column, eluting with 95:5 hexanes-acetone to yield the title compound as a light yellow solid. Mass spectrum (ESI) 287 (M+1).

Workup

  1. temperatureto reflux
  2. customAll but ca. 5 mL of POCl3 was removed by vacuum distillation
  3. customthe residue was quenched
  4. additionby pouring into 200 mL of ice-water
  5. extractionextracting with 3×100 mL of EtOAc
  6. washThe combined organics were washed with 100 mL of brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on a Biotage 40M column
  10. washeluting with 95:5 hexanes-acetone

Sources & evidence

ORD record
ord-6344ea63a6984fb2ba644e1be184b4cc
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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