58990-53-7

Basic information

• Product Name: 5-CHLORO-2,4-BIS-TRIMETHYLSILANYLOXY-PYRIMIDINE
• Synonyms: 5-CHLORO-2,4-BIS-TRIMETHYLSILANYLOXY-PYRIMIDINE;5-chloro-2,4-bis-O-trimethylsilyluracil;5-chloro-2,4-bis[(trimethylsilyl)oxy]Pyrimidine
• CAS NO: 58990-53-7
• Molecular Formula: C₁₀H₁₉ClN₂O₂Si₂
• Molecular Weight: 290.89406
• Mol File: 58990-53-7.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-CHLORO-2,4-BIS-TRIMETHYLSILANYLOXY-PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2,4-BIS-TRIMETHYLSILANYLOXY-PYRIMIDINE(58990-53-7)
• EPA Substance Registry System: 5-CHLORO-2,4-BIS-TRIMETHYLSILANYLOXY-PYRIMIDINE(58990-53-7)

Safety Data

• Hazardous Substances Data: 58990-53-7(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1820-81-1 5-chlorouracil 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 1820-81-1 2,4-dihydroxy-5-chloropyrimidine 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 

Downstream Products

• 2857-97-8 trimethylsilyl bromide 
• 81777-43-7 Acetic acid 2-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-ethyl ester 
• 141249-35-6 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-5-chlorouracil 
• 127984-94-5 1-amino-5-chlorouracil 
• 146762-17-6 1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-chlorouracil 

Relevant articles and documents

Efficient and selective catalytic N-Alkylation of pyrimidine by ammonium Sulfate?Hydro-thermal carbone under eco-friendly conditions

Abstract: An efficient and inexpensive method for the N-alkylation of pyrimidines using ammonium sulfate coated Hydro-Thermal-Carbone (HTC) (AS?HTC) as reused heterogeneous catalyst was developed. The catalyst was characterized by several analytical techniques such as SEM, XRD, and FTIR. The effect of various parameters was studied including catalyst loading, mole ratio, to achieve excellent selectivity and yields in 80–90%. Significantly, the present protocol offers the use of an inexpensive and environmentally friendly catalyst and simple workup. The simplicity of the procedure, excellent yield of the products, and the recyclability of the catalyst are the main advantages of this method. Graphic Abstract: Ammonium sulfate coated Hydro-Thermal-Carbone (HTC) (AS?HTC); an efficient and reused heterogeneous catalyst of the N-alkylation of pyrimidines was developed. Excellent selectivity and yields (80–90%) toward N1-alkylpyrimidines were achieved. Significantly, the present protocol offers the use of an inexpensive and environmentally friendly catalyst and simple workup.[Figure not available: see fulltext.]

A solid-supported acidic oxazolium perchlorate as an easy-handling catalyst for the synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation

A solid-supported acidic oxazolium perchlorate was investigated as a heterogeneous catalyst in N-glycosylation reactions using silylated modified pyrimidines and an acylated ribose or glucose to afford the corresponding pyrimidine nucleosides. This salt is a nonhygroscopic and stable powder whose activity is comparable to that of 2-methyl-5-phenylbenzoxazolium perchlorate. A reaction with this polymer catalyst can be conducted on a gram scale. Reusability of the solid-supported catalyst was also investigated.

Synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation catalyzed by 2-methyl-5-phenylbenzoxazolium perchlorate

Several acidic azolium salts prepared from oxazole, thiazole, and imidazole derivatives were investigated as catalysts in N-glycosylation reaction using a silylated modified pyrimidine and an acylated ribose or glucose to afford the corresponding pyrimidine nucleoside. Among the salts, 2-methyl-5- phenylbenzoxazolium perchlorate showed the highest catalytic activity. This salt is a nonhygroscopic crystalline compound that shows higher activity than the frequently used trimethylsilyl triflate. Reactions with this salt can be conducted in gram scales.