Chlorotrimethylsilane → HCID 178522540, compound

HRID 543665Notes

Reaction equation

HRID 543665 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.C(N(CC)CC)C.C[Si](Cl)(C)C.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)(Cl)Cl.[OH-].[Na+].O>[C:24]([NH:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 178508418HCID 178508418, compound

Product 1

HCID 178522540HCID 178522540, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Amino-4-hydroxypyrimidine-5-carboxylic acid (310 mg, 2 mmol) was suspended in chloroform (20 ml) and treated with triethylamine (880 μl, 6.2 mmol) and trimethylsilylchloride (850 μl, 6.2 mmol) at reflux for 4 hours. Benzoyl chloride (250 μl, 2 mmol) was added and the reaction mixture allowed to cool overnight. Water (10 ml) was added with very vigorous stirring and the solid product was dissolved in the aqueous layer by addition of 10% NaOH. After washing the aqueous layer with further chloroform, the product was precipitated by acidification to pH 0. The filtered product was washed with water and ether. Yield 374 mg (72%)

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureto cool overnight
  3. washAfter washing the aqueous layer with further chloroform
  4. customthe product was precipitated by acidification to pH 0
  5. washThe filtered product was washed with water and ether

Sources & evidence

ORD record
ord-cc0cdc7e9d094b4c92a04c14758d504d
Source dataset
uspto-grants-1984_05
Patent number
US04447422

Reaction notes

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