Sodium Iodide → HCID 18470371, compound

HRID 2228921Notes

Reaction equation

HRID 2228921 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([O:30]C)[CH:25]=3)=[CH:18][N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[Si](C)(C)C.[I-].[Na+]>C(#N)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]3[CH:29]=[CH:28][NH:27][C:26](=[O:30])[CH:25]=3)=[CH:18][N:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 18470163HCID 18470163, compound

Product 1

HCID 18470371HCID 18470371, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(8-phenyloct-1-yl)thio-5-(2-methoxypyrid-4-ylmethyl)pyrimidin-4-one (0.40 g, 0.9 mmol), chlorotrimethylsilane (0.23 ml, 1.8 mmol) and sodium iodide (0.27 g, 1.8 mmol) in acetonitrile (30 ml) was heated at reflux for 6 hours. The solvent was evaporated, the residue taken up in dichloromethane, and washed with water and aqueous sodium thiosulphate. Evaporation of the solvent and trituration with ether gave 2-(8-phenyloct-1-yl)thio-5-(2-oxopyrid-4-ylmethyl)pyrimidin-4-one as a white solid (0.03 g). 1H-NMR (d6-DMSO) δ 1.3 (8H, m), 1.6 (4H, m), 2.55 (2H, t), 3.07 (2H, t), 6.07 (2H, m), 7.1-7.3 (6H, m), 7.77 (1H, s); MPt indeterminate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customThe solvent was evaporated
  4. washwashed with water and aqueous sodium thiosulphate
  5. customEvaporation of the solvent and trituration with ether

Sources & evidence

ORD record
ord-43b6ef87c3c94fe2841e3579c9e952ce
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

Loading…