(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL

Base Information

• Chemical Name: (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL
• CAS No.: 588-36-3
• Molecular Formula: C₆H₉N₃OS
• Molecular Weight: 171.223
• Hs Code.: 29335990
• Mol file: 588-36-3.mol

Synonyms:(4-Amino-2-methanethiopyrimidin-5-yl)methanol;2-Methylmercapto-4-amino-5-hydroxymethylpyrimidine;2-Methylthio-4-amino-5-(hydroxymethyl)pyrimidine;4-Amino-2-methylmercapto-5-pyrimidinemethanol;4-Amino-2-methylthio-5-pyrimidinemethanol;4-Amino-5-hydroxymethyl-2-methylthiopyrimidine;NSC 3431;NSC43811;[4-Amino-2-(methylthio)pyrimidin-5-yl]methanol;(4-amino-2-(methylthio)pyrimidin-5-yl)methanol;

Chemical Property of (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL

Chemical Property:

• Vapor Pressure: 2.07E-07mmHg at 25°C
• Melting Point: 126-127°
• Refractive Index: 1.646
• Boiling Point: 408.6 °C at 760 mmHg
• PKA: 13.08±0.10(Predicted)
• Flash Point: 200.9 °C
• PSA: 97.33000
• Density: 1.38 g/cm³
• LogP: 0.85420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

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

Methioprim ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Tumor antagonist in mice. (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL is an intermediate used in the synthesis of Thiamine (T344185). Also, used for the preparation of pyridopyrimidines and naphthyridines as inhibitors of Akt kinase for the treatment of cancer.

Technology Process of (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL

There total 5 articles about (4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL 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: 98.0%

ethyl 4-amino-2-methylmercaptopyrimidine-5-carboxylate (776-53-4) → (4-amino-2-(methylthio)pyrimidin-5-yl)methanol (588-36-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jm049355+

Reference yield:

4-amino-2-(methylthio)pyrimidine-5-carboxylic acid (771-81-3) → of4-amino-2-methylthiopyrimidine-5-methanol + (4-amino-2-(methylthio)pyrimidin-5-yl)methanol (588-36-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; diethyl ether; water; ethyl acetate;

Reference yield:

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0) → (4-amino-2-(methylthio)pyrimidin-5-yl)methanol (588-36-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NH₃; triethylamine / tetrahydrofuran

2: 98 percent / LAH / tetrahydrofuran / 20 °C

With lithium aluminium tetrahydride; ammonia; triethylamine; In tetrahydrofuran;

DOI:10.1021/jm049355+

upstream raw materials:

ethyl 4-amino-2-methylmercaptopyrimidine-5-carboxylate

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

ethyl 4-amino-2-thioxo-1H-pyrimidine-5-carboxylate

4-amino-2-(methylthio)pyrimidine-5-carboxylic acid

Downstream raw materials:

4-[4-(8-isopropyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)phenyl]piperazine-1-carboxylic acid tert-butyl ester

1-(4-amino-2-methylsulfanylpyrimidin-5-yl)ethanone

5-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

8-ethyl-2-(methylsulfanyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Refernces

• 1、 Okuda,Price. "-". . p. 1719. Retrieved 1957.
• 2、 -. "SALT FORM AND CRYSTAL FORM OF NOVEL AZATRICYCLIC COMPOUND AND USE THEREOF". Paragraph 0276; 0279; 0280. . Retrieved 2021/11/05.
• 3、 -. "FGFR INHIBITOR AND APPLICATION THEREOF". Paragraph 0093; 0095. . Retrieved 2020/01/22.