Tetraethyltin → HCID 86625746, compound

HRID 1367239Notes

Reaction equation

HRID 1367239 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-e6504f2e38ba4af6aa1d0dc6c5c5988d
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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