4-(Methylamino)-2-(methylthio)pyrimidine-5-methanol
- Product Name
- 4-(Methylamino)-2-(methylthio)pyrimidine-5-methanol
- CAS No.
- 17759-30-7
- Chemical Name
- 4-(Methylamino)-2-(methylthio)pyrimidine-5-methanol
- Synonyms
- (4-MethylaMino-2-MethanethiopyriMidin-5-yl)Methanol;4-(MethylaMino)-2-(Methylthio)-5-pyriMidineMethanol;4-(Methylamino)-2-(methylthio)pyrimidine-5-methanol;5-Pyrimidinemethanol, 4-(methylamino)-2-(methylthio)-;(4-MethylaMino-2-MethylsulfanylpyriMidin-5-yl)Methanol;(4-(MethylaMino)-2-(Methylthio )pyriMidin-5-yl)Methanol;(4-MethylaMino-2-Methanesulfanyl-pyriMidin-5-yl)-Methanol
- CBNumber
- CB32510337
- Molecular Formula
- C7H11N3OS
- Formula Weight
- 185.25
- MOL File
- 17759-30-7.mol
4-(Methylamino)-2-(methylthio)pyrimidine-5-methanol Property
- Melting point:
- 155-157 °C
- Boiling point:
- 398.9±32.0 °C(Predicted)
- Density
- 1.28±0.1 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- Chloroform, Dichloromethane, DMSO, Methanol
- form
- Solid
- pka
- 13.16±0.10(Predicted)
- color
- White
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- M286900
- Product name
- 4-(Methylamino)-2-(methylthio)pyrimidine-5-methanol
- Packaging
- 100mg
- Price
- $160
- Updated
- 2021/12/16
- Product number
- CS-0018973
- Product name
- (4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanol
- Packaging
- 1g
- Price
- $400
- Updated
- 2021/12/16
- Product number
- CHM0390187
- Product name
- (4-(METHYLAMINO)-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $502.44
- Updated
- 2021/12/16
- Product number
- CS-0018973
- Product name
- (4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanol
- Packaging
- 5g
- Price
- $711
- Updated
- 2021/12/16
- Product number
- 126652
- Product name
- (4-(Methylamino)-2-(methylthio)-pyrimidin-5-yl)methanol
- Purity
- >95%
- Packaging
- 1g
- Price
- $1044
- Updated
- 2021/12/16
4-(Methylamino)-2-(methylthio)pyrimidine-5-methanol Chemical Properties,Usage,Production
Chemical Properties
White Solid
Uses
An intermediate in the preparation of antitumor agents and tyrosine kinase inhibitors
Synthesis
76360-82-2
17759-30-7
The general procedure for the synthesis of (4-methylamino-2-methanesulfonyl-pyrimidin-5-yl)-methanol from ethyl 4-methylamino-2-methylthio-5-pyrimidinecarboxylate was as follows: lithium aluminium hydride (11.48 g, 302 mmol) was suspended in 600 mL of anhydrous tetrahydrofuran (THF) in a 2 L three-necked flask fitted with an overhead stirrer, protected by argon gas. Another 250 mL round-bottomed flask was taken and ethyl 4-methylamino-2-methylthio-5-pyrimidine carboxylate (43.71 g, 0.192 mol) was dissolved in 200 mL of anhydrous THF and transferred through a cannula to a 250 mL addition funnel. The pyrimidine solution was slowly added dropwise to the lithium aluminum hydride suspension at room temperature for a controlled time of 30 minutes. After the dropwise addition was completed, the reaction was continued with stirring for 1 hour. Subsequently, 25 mL of water was carefully added dropwise over 30 minutes to quench the reaction. Next, 25 mL of 15% (w/v) aqueous sodium hydroxide solution and 75 mL of water were added sequentially, at which point the reaction mixture faded from a light green color and formed a light green slurry, and stirring was continued for 1 hour. Upon completion of the reaction, the precipitated aluminum salt was removed by vacuum filtration and the solid was washed well with ethyl acetate (EtOAc). The filtrate was concentrated to give a light yellow slurry. The slurry was suspended in 250 mL of a 25% EtOAc/hexane solvent mixture and the colorless solid was separated by vacuum filtration. After vacuum drying, 31.9 g (90% yield) of the target product (4-methylamino-2-methylthio-pyrimidin-5-yl)-methanol was obtained, and the spectral data were consistent with those reported in the literature.
References
[1] Patent: WO2004/63195, 2004, A1. Location in patent: Page 53-54
[2] Patent: WO2006/71940, 2006, A2. Location in patent: Page/Page column 355
[3] Patent: WO2008/33999, 2008, A2. Location in patent: Page/Page column 88
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2255 - 2265
[5] Patent: US2003/207900, 2003, A1. Location in patent: Page/Page column 15
4-(Methylamino)-2-(methylthio)pyrimidine-5-methanol Preparation Products And Raw materials
Raw materials
Preparation Products
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