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5-AMINO-4-CHLOROPYRIMIDINE

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5-AMINO-4-CHLOROPYRIMIDINE Basic information

Product Name:
5-AMINO-4-CHLOROPYRIMIDINE
Synonyms:
  • 5-AMINO-4-CHLOROPYRIMIDINE
  • 5-PYRIMIDINAMINE, 4-CHLORO-
  • 5-Pyrimidinamine, 4-chloro- (9CI)
  • 4-chloropyriMidin-5-aMine
  • 4-Chloro-5-aMinopyriMidine
  • 4-chloro-pyriMidin-5-ylaMine
  • 4-Chloro-5-pyrimidinamine
  • Amino chloropyrimidine
CAS:
54660-78-5
MF:
C4H4ClN3
MW:
129.55
Product Categories:
  • Heterocycle-Pyrimidine series
  • PYRIMIDINE
Mol File:
54660-78-5.mol
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5-AMINO-4-CHLOROPYRIMIDINE Chemical Properties

Melting point:
110-116℃
Boiling point:
253.8±20.0 °C(Predicted)
Density 
1.437±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
pka
1.30±0.16(Predicted)
form 
Solid
color 
White to pale brown
Sensitive 
Air & Light Sensitive
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-41
Safety Statements 
26-39
WGK Germany 
3
HS Code 
29335990
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5-AMINO-4-CHLOROPYRIMIDINE Usage And Synthesis

Synthesis

54851-35-3

54660-78-5

General procedure for the synthesis of 5-amino-4-chloropyrimidine from 5-amino-6-chloropyrimidine-4-thiol: The concentrated product of Example 18 (4.3 g, 26 mmol) was dissolved in EtOH (40 mL). Subsequently, NH4OH (4 mL) was added to this solution. Under stirring, an excess of Raney Nickel was added in batches. the reaction mixture was stirred overnight at room temperature and then heated at 80 °C for 2 h. The reaction was carried out at room temperature. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filtrate was concentrated. The crude product was purified by silica fast chromatography using EtOAc/hexane as eluent to give 1.6 g (47% yield) of 5-amino-4-chloropyrimidine as a yellow solid.

References

[1] Patent: US2006/13799, 2006, A1. Location in patent: Page/Page column 59
[2] Patent: WO2006/127584, 2006, A1. Location in patent: Page/Page column 61; 89
[3] Patent: WO2007/8563, 2007, A2. Location in patent: Page/Page column 88

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