2-Chloro-5-hydroxypyrimidine Chemical Properties

Melting point:

195-196 °C

Boiling point:

328.1±15.0 °C(Predicted)

Density 

1.513±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

6.17±0.23(Predicted)

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C4H3ClN2O/c5-4-6-1-3(8)2-7-4/h1-2,8H

InChIKey

BOGPIHXNWPTGNH-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(O)C=N1

CAS DataBase Reference

4983-28-2(CAS DataBase Reference)

Safety Information

HS Code 

29335990

2-Chloro-5-hydroxypyrimidine Usage And Synthesis

Uses

2-Chloro-5-hydroxypyrimidine is an intermediate used to synthesize tandospirone derivatives with anxiolytic activities.

Synthesis

2-Chloro-5-methoxypyrimidine (0.46 g, 3.18 mmol) in methylene chloride (10 mL) was treated with 1.0 N boron tribromide (16 mL, 16 mmol) at room temperature. The solution was stirred overnight. After that, the reaction was partitioned between saturated NaHCO3 and DCM. The aqueous layer was extracted with additional DCM. Combined the organic layers and dried (MgSO4), filtered, and concentrated to obtain the crude product. The residue was purified by flash column chromatography on silica gel to give 2-Chloro-5-hydroxypyrimidine.

References

[1] Patent: WO2010/80503, 2010, A1. Location in patent: Page/Page column 225
[2] Patent: WO2011/144578, 2011, A1. Location in patent: Page/Page column 27
[3] Patent: WO2011/144577, 2011, A1. Location in patent: Page/Page column 24-25
[4] Patent: WO2016/164703, 2016, A1. Location in patent: Page/Page column 50
[5] Patent: US5589478, 1996, A

2-Chloro-5-hydroxypyrimidine(4983-28-2)Related Product Information

• HYDROXYAPATITE TYPE I
• Glycolic acid
• 2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL
• Sulfadiazine
• 2-Chloropyrimidine
• Uracil
• Hydroxy silicone oil
• Chrysin
• Silver sulfadiazine
• 4-Hydroxybenzaldehyde
• 5-Hydroxypyrimidine
• 2-Chloro-5-fluoropyrimidine
• Tandospirone
• 1-N-Boc-4-pyriMidin-2-yl-piperazine
• (3aR,4R,7S,7aS)-2-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]hexahydro-1H-4,7-methanoisoindole-1,3-dione
• Difluorochloromethane
• Camptothecin Series--10-hydroxycamptothecin
• 2,4-Dichloro-5-methoxypyrimidine