Triethylamine → HCID 86082260, compound

HRID 645537Notes

Reaction equation

HRID 645537 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][C:8]1[CH:9]=[C:10]([CH2:14]O)[CH:11]=[CH:12][CH:13]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:28]=[N+:29]=[N-:30].[Na+]>ClCCl.O>[N:28]([CH2:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[O:7][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[N+:29]=[N-:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 2763397[3-(2-pyrimidinyloxy)phenyl]methanol

Product 1

HCID 86082260HCID 86082260, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 3-(pyrimidin-2-yloxy)-phenyl-methanol (500 mg, 2.47 mmol) and triethylamine (625 μL, 4.5 mmol) in dichloromethane (40 mL) was added MsCl (2.33 uL, 3.0 mmol) at 0° C. The reaction was kept at 0° C. for 15 min. Removal of the solvent, the residue was dissolved in N,N-dimethylformamide (30 mL) and then treated with sodium azide (803 mg, 12.4 mmol). The reaction mixture was heated at 80° C. for 4 hr. The reaction mixture was poured into water, and extracted with ethyl acetate (2×). The solvent was removed, and the resulting residue was chromatographered using hexane/ethyl acetate (2:1) to give the title compound (483 mg, 86%). MS (DCI/NH3) m/z 228 (M+1)+. 1H NMR (500 MHz, DMSO-d6) δ ppm 4.49 (s, 2H) 7.19 (dd, J=8.11, 2.18 Hz, 1H) 7.21 (t, J=1.87 Hz, 1H) 7.26 (d, J=7.18 Hz, 1H) 7.27 (t, J=4.68 Hz, 1H) 7.47 (t, J=7.80 Hz, 1H) 8.64 (s, 1H) 8.65 (s, 1H).

Workup

  1. customRemoval of the solvent
  2. dissolutionthe residue was dissolved in N,N-dimethylformamide (30 mL)
  3. extractionextracted with ethyl acetate (2×)
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-3f86610f689b42e0873a4a6409c7c27b
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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