5-AMINO-2-(METHYLTHIO)PYRIMIDINE-4-CARBOXYLIC ACID

Base Information

• Chemical Name: 5-AMINO-2-(METHYLTHIO)PYRIMIDINE-4-CARBOXYLIC ACID
• CAS No.: 100130-05-0
• Molecular Formula: C₆H₇N₃O₂S
• Molecular Weight: 185.206
• Hs Code.: 2933599090
• Mol file: 100130-05-0.mol

Synonyms:5-Amino-2-(methylthio)pyrimidine-4-carboxylicacid;

Chemical Property of 5-AMINO-2-(METHYLTHIO)PYRIMIDINE-4-CARBOXYLIC ACID

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 190-191.5℃ (decomposition)
• Refractive Index: 1.668
• Boiling Point: 434.973 °C at 760 mmHg
• PKA: 3.40±0.10(Predicted)
• Flash Point: 216.864 °C
• PSA: 114.40000
• Density: 1.538 g/cm³
• LogP: 1.06010
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Amino-2-(methylthio)pyrimidine-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5-Amino-2-(methylthio)pyrimidine-4-carboxylic acid is a versatile reactant used in the preparation of helicene analogs.

Technology Process of 5-AMINO-2-(METHYLTHIO)PYRIMIDINE-4-CARBOXYLIC ACID

There total 2 articles about 5-AMINO-2-(METHYLTHIO)PYRIMIDINE-4-CARBOXYLIC ACID 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: 90.0%

5-bromo-2-methylsulfanyl-pyrimidine-4-carboxylic acid (50593-92-5) → 5-amino-2-methylsulfanylpyrimidine-4-carboxylic acid (100130-05-0)

Guidance literature:

With ammonium hydroxide; copper(II) sulfate; at 95 ℃; for 5.5h; under 3750.38 Torr;

DOI:10.1002/ejoc.202100593

Reference yield:

5-bromo-2-methylsulfanyl-pyrimidine-4-carboxylic acid (50593-92-5) + copper(II) sulfate (7758-99-8) → 5-amino-2-methylsulfanylpyrimidine-4-carboxylic acid (100130-05-0)

Guidance literature:

With ammonia; In hydrogenchloride; sodium hydroxide; water;

Reference yield:

5-amino-2-methylsulfanylpyrimidine-4-carboxylic acid (100130-05-0) → 7-((tert-butoxycarbonyl)(6-methyl-2-(methylthio)pyrido[3,2-d]pyrimidin-7-yl)amino)-2-(methylthio)pyrido[3,2-d]pyrimidin-6-yl 4-methylbenzenesulfonate

Guidance literature:

Multi-step reaction with 7 steps

1.1: tetrahydrofuran; diethyl ether / 0.5 h / 0 - 20 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran / -20 - 20 °C

3.1: manganese(IV) oxide / acetonitrile / 2 h / 20 °C

4.1: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0.25 h / -20 °C

4.2: 16 h / -20 - 20 °C

5.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1,4-dioxane / 8.5 h / 105 °C

6.1: dmap / tetrahydrofuran / 5.5 h / 0 - 20 °C

7.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.1 h / 0 °C

With dmap; manganese(IV) oxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 18-crown-6 ether; potassium tert-butylate; diisobutylaluminium hydride; caesium carbonate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; diethyl ether; acetonitrile; 4.1: |Horner-Wadsworth-Emmons Olefination / 4.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1002/ejoc.202100593

upstream raw materials:

5-bromo-2-methylsulfanyl-pyrimidine-4-carboxylic acid

copper(II) sulfate

Downstream raw materials:

6-methylsulfanyl-3H-pyrimido[5,4-d]pyrimidin-4-one

4-hydroxy-6-methylthio-pyrimido[5,4-d]pyrimidine

4-[(3-Chloro-4-fluoro-phenyl)amino]-6-methylthio-pyrimido[5,4-d]pyrimidine

Refernces

• 1、 Hofmann, Philipp E.,Meinecke, Jannick,Harms, Klaus,Koert, Ulrich. "Synthesis and Functionalization of C6/C7 Substituted Pyrido[3,2-d]pyrimidines". . p. 6263 - 6281. Retrieved 2021.
• 2、 -. "Pyrimido?5,4-D!pyrimidines, medicaments comprising these compounds, their use and processes for their preparation". . . Retrieved 2008/06/13.