Tetraethyltin → HCID 86625746, compound

HRID 1864916Notes

Reaction equation

HRID 1864916 reaction equation
Cl[C:2]1[C:3](=[O:26])[N:4]([CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([Cl:8])[N:7]=1.[CH2:27]([Sn](CC)(CC)CC)[CH3:28]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:6]1[N:7]=[C:2]([CH2:27][CH3:28])[C:3](=[O:26])[N:4]([CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 11704TetraethyltinHCID 11132878HCID 11132878, compound

Product 1

HCID 86625746HCID 86625746, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of benzyl (3,5-dichloro-2-oxo-6-phenylpyrazin-1 (2H)-yl)acetate [Parlow et al. (2003) J. Med. Chem. 46, 4050-4062] (1.05 g, 2.70 mmol), tetraethyltin (0.641 mL, 3.24 mmol), and tetrakis(triphenylphosphine)palladium (31.0 mg, 0.027 mmol) in toluene (15 mL) was heated at reflux for 5.5 h. The solution was concentrated in vacuo and the crude product purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc-100:0 to 90:10 to give the title compound. MS: m/z=383 (M+1).

Workup

  1. temperatureat reflux for 5.5 h
  2. concentrationThe solution was concentrated in vacuo
  3. customthe crude product purified by silica gel chromatography
  4. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-b54e534b519840e69c2fb1f87e73d4ee
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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