(Diethylamino)sulfur trifluoride → HCID 59525687, compound

HRID 386090Notes

Reaction equation

HRID 386090 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]O)[N:3]=1.CCN(S(F)(F)[F:16])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][F:16])[N:3]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 55273715(4-Chloropyrimidin-2-yl)methanol

Product 1

HCID 59525687HCID 59525687, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(4-Chloropyrimidin-2-yl)methanol (Example 548, Step 1) (121 mg, 0.84 mmol) was taken up in DCM (2.5 mL) and cooled to 0° C. DAST (0.122 mL, 0.92 mmol) was added and the resulting mixture stirred at 0° C. for 15 minutes and room temperature for 90 minutes. Saturated NaHCO3 was added and the products extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (2-40% EtOAc-hexanes) gave the title compound as a pale yellow oil.

Workup

  1. extractionthe products extracted into EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by silica gel chromatography (2-40% EtOAc-hexanes)

Sources & evidence

ORD record
ord-cb58b635dec24c9a9727a38f16965721
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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