Pyrimidine, 4,6-dichloro-5-[(phenylmethyl)thio]-

Base Information

• Chemical Name: Pyrimidine, 4,6-dichloro-5-[(phenylmethyl)thio]-
• CAS No.: 138918-24-8
• Molecular Formula: C11H8Cl2N2S
• Molecular Weight: 271.17
• DSSTox Substance ID: DTXSID80474184
• Nikkaji Number: J962.182B

Synonyms:138918-24-8;Pyrimidine, 4,6-dichloro-5-[(phenylmethyl)thio]-;SCHEMBL9426904;DTXSID80474184

Chemical Property of Pyrimidine, 4,6-dichloro-5-[(phenylmethyl)thio]-

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 269.9785248
• Heavy Atom Count: 16
• Complexity: 202

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CSC2=C(N=CN=C2Cl)Cl

Technology Process of Pyrimidine, 4,6-dichloro-5-[(phenylmethyl)thio]-

There total 4 articles about Pyrimidine, 4,6-dichloro-5-[(phenylmethyl)thio]- 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: 72.0%

4,6-dihydroxy-5-benzylthiopyrimidine (138918-23-7) → 4,6-dichloro-5-benzylthiopyrimidine (138918-24-8)

Guidance literature:

With trichlorophosphate; for 3h; Heating;

DOI:10.1080/00397919308011121

Reference yield:

4,6-dihydroxy-5-benzylthiopyrimidine (138918-23-7) → 2,6-Dichloropyrimidine (3934-20-1) + 4,6-dichloro-5-benzylthiopyrimidine (138918-24-8)

Guidance literature:

With trichlorophosphate; In chloroform;

Reference yield:

phenylmethanethiol (100-53-8) → 4,6-dichloro-5-benzylthiopyrimidine (138918-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / potassium carbonate / dimethylformamide / 3.5 h / 95 - 105 °C

2: 72 percent / POCl₃ / 3 h / Heating

With potassium carbonate; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.1080/00397919308011121

upstream raw materials:

4,6-dihydroxy-5-benzylthiopyrimidine

dibenzyl disulphide

phenylmethanethiol

Downstream raw materials:

4,6-diethoxy-5-benzylthiopyrimidine

Refernces

A convenient synthesis of 4,6-dichloro-5-benzylthiopyrimidine

10.1080/00397919308011121

The study presents a practical and convenient two-step synthesis of the title compound, 4,6-dichloro-5-benzylthiopyrimidine (3), starting from 4,6-dihydroxypyrimidine (1). The initial three-step approach involved converting 4,6-dihydroxypyrimidine (1) to 4,6-dihydroxy-5-bromopyrimidine (4) with an 80% yield. Then, compound (4) was reacted with benzylmercaptan and anhydrous potassium carbonate in N,N-dimethylformamide, yielding 4,6-dihydroxy-5-benzylthiopyrimidine (2) with a variable yield, the best being 50%. Finally, compound (2) was converted to the title compound (3) by heating in phosphorus oxychloride, resulting in a 75% yield. An improved method was developed using sulfenyl chloride chemistry, where benzyl sulfenyl chloride was prepared from dibenzyl disulfide and sulfuryl chloride, and reacted with 4,6-dihydroxypyrimidine (1) in N,N-dimethylformamide to obtain compound (2) in quantitative yield. The title compound (3) was then synthesized from compound (2) using phosphorus oxychloride, achieving an overall yield of approximately 72%. The study provides a more efficient and reliable synthesis route for 4,6-dichloro-5-benzylthiopyrimidine, which is a key precursor in the synthesis of various types of 4,6-di-substituted pyrimidine-5-sulfonamides with interesting biological activities.

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