ethyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Base Information

• Chemical Name: ethyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• CAS No.: 482655-63-0
• Molecular Formula: C₂₀H₃₀N₂O₃SSi
• Molecular Weight: 406.621
• Mol file: 482655-63-0.mol

Synonyms:ethyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Chemical Property of ethyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

There total 4 articles about ethyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

tert-butyldimethylsilyl chloride (18162-48-6) + monastrol (329689-23-8,254753-54-3,268739-54-4) → ethyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (482655-63-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(02)01269-8

Reference yield:

meta-hydroxybenzaldehyde (100-83-4) → ethyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (482655-63-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Yb(OTf)3 / tetrahydrofuran / 12 h / Heating

2: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

With 1H-imidazole; ytterbium(III) triflate; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Biginelli cyclocondensation reaction;

DOI:10.1016/S0040-4039(02)01269-8

Reference yield:

ethyl acetoacetate (141-97-9) → ethyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (482655-63-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Yb(OTf)3 / tetrahydrofuran / 12 h / Heating

2: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

With 1H-imidazole; ytterbium(III) triflate; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Biginelli cyclocondensation reaction;

DOI:10.1016/S0040-4039(02)01269-8

upstream raw materials:

tert-butyldimethylsilyl chloride

monastrol

ethyl acetoacetate

meta-hydroxybenzaldehyde

Downstream raw materials:

(S)-monastrol

(-)-4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester

(R)-3-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-carbonyl)-4-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester

(S)-3-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-carbonyl)-4-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester