6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol Chemical Properties

Melting point:

193-196°C

Boiling point:

336.0±52.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Methanol (Slightly)

form 

Solid

pka

10.08±0.50(Predicted)

color 

Off-White

6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol Usage And Synthesis

Chemical Properties

White Crystals With a Greenish Cast

Synthesis

Step i: 6-Amino-5-(2,2-diethoxyethyl)-2-mercapto-4-hydroxypyrimidine (11.6 mmol) [for preparation, see Davoll, J., J. Chem. Soc., 1960, pp131-138] was dissolved in a solvent mixture of water (150 mL) and aqueous ammonia solution (9 mL) and heated to 90°C. Raney Nickel suspension was added to the reaction mixture in batches (2-3 mL at a time) until TLC and LC/MS analysis showed that the reaction was complete. The reaction mixture was cooled to room temperature, filtered through a diatomaceous earth pad and the filter cake was washed with water (2 x 25 mL). The combined aqueous filtrates were freeze-dried to afford 6-amino-5-(2,2-diethoxyethyl)-4-hydroxypyrimidine as an off-white powder in a yield of 2.23 g (85%).LC/MS: RT = 1.37 min; m/z = 182 [M-EtOH + H]+ . Total run time was 3.75 min.1H NMR (DMSO-d6): δ 1.07 (t, 6H); 3.40 (m, 2H); 3.59 (m, 2H); 4.56 (t, 1H); 6.07 (br s, 2H); 7.70 (s, 1H); 11.43 (br s, 1H).

References

[1] Patent: WO2007/104944, 2007, A1. Location in patent: Page/Page column 43
[2] Patent: WO2006/46023, 2006, A1. Location in patent: Page/Page column 123
[3] Patent: WO2008/75109, 2008, A1. Location in patent: Page/Page column 112
[4] Patent: WO2006/46024, 2006, A1. Location in patent: Page/Page column 118
[5] Patent: WO2007/125321, 2007, A2. Location in patent: Page/Page column 116

6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol(7400-06-8)Related Product Information

• Tofacitinib impurity T
• Methyl (4-Methylpiperidin-3-yl)carbaMate
• 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
• 6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE
• 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
• Tofacitinib Impurity 19