6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE Chemical Properties

Melting point:

>300°C

Density 

1.27

storage temp. 

-20°C Freezer

solubility 

DMSO, Methanol

pka

8.08±0.25(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Sensitive to Aqueous Acid

CAS DataBase Reference

7400-05-7

Safety Information

Risk Statements 

22-40

Safety Statements 

36/37

HS Code 

29335990

6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

Intermediate in the production of thymidine phosphorylase inhibitors.

Synthesis

To a freshly prepared sodium ethanolate solution [made by reacting ethanol (250 mL) with sodium metal (9.02 g, 392.55 mmol)], ethyl 2-cyano-4,4-diethoxybutyrate (45 g, 196.27 mmol) and thiourea (14.94 g, 196.27 mmol dissolved in 200 mL of ethanol) were added sequentially. The reaction mixture was heated to reflux for 3.5 hours with stirring. Upon completion of the reaction, the mixture was cooled to room temperature and stirring was continued overnight. Subsequently, the reaction was quenched with water (100 mL) and the ethanol was removed by vacuum concentration. The residue was dissolved in water (100 mL) and neutralized with dilute aqueous hydrochloric acid (3N) to pH 7 at a temperature below 10 °C. The resulting solid was collected by filtration and dried under vacuum to afford 6-amino-5-(2,2-diethoxyethyl)-2-mercapto-pyrimidin-4-ol (30.6 g, 60.19% yield) as a light yellow solid. The product was confirmed by 1HNMR, IR, MS, HPLC and elemental analysis.

References

[1] Patent: WO2010/14930, 2010, A2. Location in patent: Page/Page column 60
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 22, p. 6770 - 6789
[3] Patent: WO2006/46023, 2006, A1. Location in patent: Page/Page column 122-123
[4] Patent: WO2008/75109, 2008, A1. Location in patent: Page/Page column 112
[5] Patent: WO2006/46024, 2006, A1. Location in patent: Page/Page column 117

6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE(7400-05-7)Related Product Information

• 1-Benzyl-4-methyl-piperidin-3-one hydrochloride
• CYANOACETIC ACID-OSU
• N-Hydroxysuccinimide
• Tofacitinib Impurity 29
• N-Methyl-N-((3S,4S)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine
• 4-(Hydroxyamino)-4-oxobutanoic acid
• 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• BENZYL ETHYL ETHER
• 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine
• N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• Tofacitinib Impurity 85
• N-((3R,4S)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• 4-Amino-2,6-dichloropyrimidine
• Malonyl chloride
• Benzyl chloride
• Methyl (4-Methylpiperidin-3-yl)carbaMate
• Tofacitinib impurity T
• Tofacitinib Impurity 19