Dichloromethane → HCID 57427822, compound

HRID 2353727Notes

Reaction equation

HRID 2353727 reaction equation
P(Cl)(Cl)([Cl:3])=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][C:15]2[NH:20][C:19](=O)[NH:18]C(=O)[CH:16]=2)=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+].[CH2:28]([Cl:30])Cl>>[Cl:3][C:19]1[N:18]=[C:28]([Cl:30])[CH:16]=[C:15]([CH2:14][S:13][C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=2)[N:20]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 57427823HCID 57427823, compound

Product 1

HCID 57427822HCID 57427822, compound

Procedure

Phosphorus oxychloride (15.2 g, 99.1 mmol) was added to 6-[(4-fluorophenyl)sulfanylmethyl]-1H-pyrimidine-2,4-dione (2.5 g, 9.91 mmol), and the resulting solution was stirred at reflux for 7 hours. The reaction was allowed to cool and the phosphorus oxychloride removed under reduced pressure to give a brown oil. This was dissolved in DCM and ice water (50 mL) added followed by solid sodium bicarbonate (until effervescence stops). The aqueous layer was extracted with DCM (2×50 mL) and the organics dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in isohexane, to give the desired material as a yellow gum (2.11 g).

Workup

  1. temperatureat reflux for 7 hours
  2. temperatureto cool
  3. customthe phosphorus oxychloride removed under reduced pressure
  4. customto give a brown oil
  5. extractionThe aqueous layer was extracted with DCM (2×50 mL)
  6. dry with materialthe organics dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto afford crude product
  10. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-a14bc16f034e46cfabe8ebdedf2d76f1
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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