Sodium Iodide → HCID 59553886, compound

HRID 1170921Notes

Reaction equation

HRID 1170921 reaction equation
Cl[C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])=[N:7][C:6]=2[CH:5]=[CH:4][N:3]=1.C[Si](Cl)(C)C.[I-:34].[Na+].[OH-].[Na+]>C(#N)CC>[I:34][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])=[N:7][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 59553904HCID 59553904, compound

Product 1

HCID 59553886HCID 59553886, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

A mixture of 5-chloro-2-(2-methoxy-phenyl)-3-phenethyl-3H-pyrido[4,3-d]pyrimidin-4-one (300 mg, 0.766 mmol), trimethylsilyl chloride (0.097 mL, 0.766 mmol) and sodium iodide (344 mg, 2.297 mmol, 3 equiv.) in propionitrile (7.66 mL) was heated to reflux under nitrogen in the dark for 4 hours. TLC showed no starting material remaining. The reaction mixture was cooled to ambient temperature and poured into 1N NaOH (30 mL). The resulting suspension was extracted with ethyl acetate (3×20 mL), the combined extracts were washed with water, brine and dried, filtered and concentrated in vacuo to give a brown oil. The crude product was purified by column chromatography using 10% ethyl acetate in dichloromethane to provide 235 mg (64%) of product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen in the dark for 4 hours
  3. extractionThe resulting suspension was extracted with ethyl acetate (3×20 mL)
  4. washthe combined extracts were washed with water, brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a brown oil
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c8c4934a73d645da9f17d4025d31cd6d
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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