176519-55-4

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione, 5-(1-methylethyl)-6-(phenylmethyl)-
• CAS NO: 176519-55-4
• Molecular Formula: C14H16N2O2
• Molecular Weight: 244.293
• Mol File: 176519-55-4.mol

Chemical Properties

• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione, 5-(1-methylethyl)-6-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione, 5-(1-methylethyl)-6-(phenylmethyl)-(176519-55-4)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione, 5-(1-methylethyl)-6-(phenylmethyl)-(176519-55-4)

Safety Data

• Hazardous Substances Data: 176519-55-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4(1H,3H)-Pyrimidinedione, 5-(1-methylethyl)-6-(phenylmethyl)is used as a key intermediate in the synthesis of various pharmaceuticals for its potential medicinal properties. Its unique structure allows for the development of novel drug candidates with improved therapeutic effects and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical industry, 2,4(1H,3H)-Pyrimidinedione, 5-(1-methylethyl)-6-(phenylmethyl)is utilized in the synthesis of agrochemicals, such as pesticides and herbicides, due to its potential biological activities. Its unique structure and properties enable the development of more effective and environmentally friendly agrochemicals.
Used in Research and Development:
2,4(1H,3H)-Pyrimidinedione, 5-(1-methylethyl)-6-(phenylmethyl)is also used in research and development within the pharmaceutical industry. It serves as a valuable compound for the discovery of novel drug candidates, as its unique structure and properties can be further modified and optimized to enhance their therapeutic potential and selectivity.

Upstream product

• 176519-53-2 ethyl 2-isopropyl-3-oxo-4-phenylbutanoate 
• 718-08-1 ethyl 3-oxo-4-phenylbutyrate 
• 103-80-0 phenylacetyl chloride 
• 199851-91-7 6-benzyl-5-isopropyl-2-thiouracil 
• 140-29-4 phenylacetonitrile 
• 609-12-1 ethyl 2-bromoisovalerate 
• 6921-34-2 benzylmagnesium chloride 
• 225232-14-4 6-benzyl-2,4-dichloro-5-isopropylpyrimidine 
• 1780-42-3 2,4,6-trichloro-5-isopropylpyrimidine 
• 909546-83-4 2-(4-bromo-2,6-dimethoxypyrimidin-5-yl)propan-2-ol 
• 909546-84-5 4-bromo-5-isopropyl-2,6-dimethoxypyrimidine 
• 96796-80-4 5-isopropyl-6-chloro-2,4-pyrimidinedione 
• 7391-69-7 5-isopropylbarbituric acid 
• 936945-30-1 6-iodo-5-isopropylpyrimidine-2,4(1H,3H)-dione 

Downstream Products

• 149950-60-7 Emivirine 
• 175739-42-1 6-benzyl-1-[(benzyloxy)methyl]-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1254831-91-8 6-benzyl-1-(((4-fluorobenzyl)oxy)methyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1254831-80-5 6-benzyl-1-(benzyloxymethyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1254831-85-0 3-amino-6-benzyl-1-(benzyloxymethyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 881887-18-9 6-benzyl-5-isopropyl-1-((Z)-4-p-toluoyloxy-2-buten-1-yloxymethyl)uracil 
• 1026714-30-6 6-benzyl-1-(ethoxymethyl)-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 165960-84-9 6-benzyl-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 1281859-62-8 6-benzyl-1-(((4-fluorobenzyl)oxy)methyl)-5-isopropyl-3-methylpyrimidine-2,4(1H,3H)-dione 
• 1281859-92-4 6-benzyl-1-(4-(4-fluorophenyl)butyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-91-3 6-benzyl-1-(3-(4-fluorophenyl)propyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

Synthesis and Antiviral Evaluation of 1-[(2-Phenoxyethyl)oxymethyl] and 6-(3,5-Dimethoxybenzyl) Analogues of HIV Drugs Emivirine and TNK-651

Novel emivirine analogues 6a, b were synthesized by reacting chloromethyl ethyl ether with 5-ethyl/isopropyl-6-(3,5-dimethoxybenzyl)uracils 5e, f. On the other hand, A series of new TNK-651 analogues 10a-f substituted at N-1 with phenoxyethoxymethyl moiety was prepared on treatment of the corresponding uracils 5a-f with bis(phenoxyethoxy)methane (9). The newly synthesized non-nucleosides were tested for antiviral activity against wild type HIV-1 IIIB as well as the resistant strains N119 (Y181C), A17 (K103N+Y181C), and the triple mutant EFVR (K103R+V179D+P225H) in MT-4 cells. Most of the tested compounds showed good activities. Among them 6-(3,5-dimethylbenzyl)-5-ethyl-1-[(2-phenoxyethyl)oxymethyl]uracil (10c) and 6-(3,5-dimethylbenzyl)-5-isopropyl-1-[(2-phenoxyethyl)oxymethyl]uracil (10d) that showed inhibitory potency higher than emivirine against both wild type HIV-1 and the tested mutant strains, as well as higher activity than efavirenz against EFVR.

New efficient and flexible synthetic route to Emivirine and its analogs

A revised synthetic route to Emivirine (MKC-442) via properly substituted β-keto ester converted from Meldrum's Acid was developed. This method could be applied to the synthesis of a variety of MKC-442 analogues and open the way for their systematic biological evaluation.

N-3 hydroxylation of pyrimidine-2,4-diones yields dual inhibitors of HIV reverse transcriptase and integrase

A new molecular scaffold featuring an N-hydroxyimide functionality and capable of inhibiting both reverse transcriptase (RT) and integrase (IN) of human immunodeficiency virus (HIV) was rationally designed based on 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) non-nucleoside RT inhibitors (NNRTIs). The design involves a minimal 3-N hydroxylation of the pyrimidine ring of HEPT compound to yield a chelating triad which, along with the existing benzyl group, appeared to satisfy major structural requirements for IN binding. In the mean time, this chemical modification did not severely compromise the compound's ability to inhibit RT. A preliminary structure-activity relationship (SAR) study reveals that this N-3 OH is essential for IN inhibition and that the benzyl group on N-1 side chain is more important for IN binding than the one on C-6.

Functionalization of unprotected uracil derivatives using the halogen - Magnesium exchange

The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl-LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5

Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine

A novel route for the synthesis of 4,5-difunctionalized uracils using a chemo- and regioselective bromine/magnesium exchange reaction on 5-bromo-4-halogeno-2,6-dimethoxypyrimidines has been developed. Applications to the synthesis of pharmaceuticals such as oxypurinol and emivirine are reported.

Method for preparing 5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1h,3h)-dione

The invention relates to a process for the preparation of 5-(1-methylethyl)-6 -(phenylmethyl)pyrimidine-2,4(1H,3H)-dione.

Regioselective alkylation and arylation at the 6-position of pyrimidine: Synthesis of 5-alkyl-6-arylmethyl-2,4-pyrimidinediones

5-Alkyl-2,4,6-trichloropyrimidines reacted with various nucleophiles to afford the regioselectivity 6-substituted pyrimidines as the major products in good yields, which were transformed to 5-alkyl-6-arylmethyl-2,4- pyrimidinediones of a key intermediate

Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine

Ethyl 2-alkyl-4-aryl-3-oxobutyrates were synthesized from the corresponding arylacetonitriles and 2-brome esters. Condensation of the butyrates with thiourea followed by treatment with chloroacetic acid afforded the 5-alkyl-6-(arylmethyl)uracils. Condensa