(Diethylamino)sulfur trifluoride → HCID 59525671, compound

HRID 386086Notes

Reaction equation

HRID 386086 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[CH2:15]O)[N:3]=1.CCN(S(F)(F)[F:23])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[CH2:15][F:23])[N:3]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 59525629{4-[(4-Chloropyrimidin-2-yl)methyl]morpholin-3-yl}methanol

Product 1

HCID 59525671HCID 59525671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

{4-[(4-Chloropyrimidin-2-yl)methyl]morpholin-3-yl}methanol (200 mg, 0.821 mmol) was taken up in DCM (4 mL) and cooled to 0° C. DAST (0.119 mL, 0.903 mmol) was added and the resulting mixture stirred at 0° C. 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 (12-100% EtOAc-hexanes) followed by HPLC (10-40% MeCN—H2O) gave the title compound as a pale yellow gum.

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 (12-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-61df5067bea54e45a2665206e6dbda5d
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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