(Diethylamino)sulfur trifluoride → HCID 25213477, compound

HRID 2194795Notes

Reaction equation

HRID 2194795 reaction equation
[CH2:1]([N:3]1[C:8]([CH:9](O)[C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([CH3:18])[CH:17]=2)[C:13]#[N:14])=[C:7]([CH:20]([CH3:22])[CH3:21])[C:6](=[O:23])[NH:5][C:4]1=[O:24])[CH3:2].C(N(S(F)(F)[F:31])CC)C>ClCCl>[CH2:1]([N:3]1[C:8]([CH:9]([F:31])[C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([CH3:18])[CH:17]=2)[C:13]#[N:14])=[C:7]([CH:20]([CH3:22])[CH3:21])[C:6](=[O:23])[NH:5][C:4]1=[O:24])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 25213707HCID 25213707, compound

Product 1

HCID 25213477HCID 25213477, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(3-Ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-hydroxy-methyl]-5-methyl-benzonitrile (100) (55.7 mg, 0.17 mmol) in dichloromethane (2.0 mL) at 0° C. was added (diethylamino)sulfur trifluoride (33 μL, 0.255 mmol) and reaction mixture stirred for 1 h. The reaction mixture was quenched with saturated NaHCO3 solution and extracted with ethyl acetate (2×). The combined organic layer was dried (MgSO4), concentrated and purified by reverse phase HPLC (Phenomenex Synergi® column, 5 to 100% acetonitrile/H2O) to give a white powder after lyophilization (45 mg, 80%). 1H NMR (300 MHz, CD3OD): 7.60 (s, 1H), 7.55 (s, 1H), 7.46 (s, 1H), 7.04 (d, J=45.9 Hz, 1H), 3.75-3.57 (m, 2H), 2.94-2.89 (m, 1H), 2.40 (s, 3H), 1.24 (d, J=6.9 Hz, 3H), 1.1-1.0 (s, 6H); %). 19F NMR (CD3OD): −180.5; Mass Spectrum: 330.1 (M+H).

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by reverse phase HPLC (Phenomenex Synergi® column, 5 to 100% acetonitrile/H2O)
  6. customto give a white powder after lyophilization (45 mg, 80%)

Sources & evidence

ORD record
ord-e587aa106f524e4a82b9fdc9ba2708ee
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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