N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide Chemical Properties

Melting point:

>251°C (dec.)

Boiling point:

554.8±60.0 °C(Predicted)

Density 

1.742±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO, Methanol

form 

Solid

pka

10.90±0.70(Predicted)

color 

Off-White to Pale Beige

InChI

InChI=1S/C5H4Cl2N4O/c6-3-2(9-1-12)4(7)11-5(8)10-3/h1H,(H,9,12)(H2,8,10,11)

InChIKey

XYWHZUCZNRMJGO-UHFFFAOYSA-N

SMILES

C(NC1=C(Cl)N=C(N)N=C1Cl)=O

CAS DataBase Reference

171887-03-9(CAS DataBase Reference)

Safety Information

HS Code 

2933.59.9500

N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide (Abacavir - In House Impurity) is an intermediate of Abacavir (A105000). Abacavir is a carbocyclic 2''-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.

Uses

Prasugrel intermediate

Uses

Abacavir intermediate. A purine derivative

Synthesis

1. 2,5-diamino-4,6-dichloropyrimidine (0.01 mol, 2.0 g) was mixed with water (0.25 mol, 4.55 mL) at room temperature and stirred. 2. 98% formic acid (0.4 mol, 18.27 g, 14.97 mL) was slowly added to the reaction system. 3. The reaction mixture was heated to 50-55 °C and maintained at this temperature for 3 hours. 4. Upon completion of the reaction, toluene (0.38 mol, 34.6 g, 40 mL) was added to the reaction system at 50 °C for azeotropic distillation. This process was repeated once, using a total of 80 mL of toluene to ensure adequate distillation. 5. After the reaction mixture was cooled, the solid product was collected by filtration and washed with cold water. 6. The washed product was dried under vacuum at 60°C. 7. 7. 2-amino-4,6-dichloro-5-formamidopyrimidine (0.01 mol, 2.0 g) was finally obtained in about 90% yield.

References

[1] Patent: EP1188750, 2002, A1. Location in patent: Page 5

N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide(171887-03-9)Related Product Information

• ALTRENOGEST
• 4,6-Dichloropyrimidine
• 2-Amino-4,6-dichloropyrimidine
• p-Aminobenzamide
• Benzamide
• Dichloroacetic acid
• 6-Aminocaproic acid
• Formamide
• Glycine
• Chlorantraniliprole
• 2-Aminopyrimidine
• N,N-Dimethylformamide
• 5-Cyanophthalide
• 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride
• 1,2,3-Triacetyl-5-deoxy-D-ribose
• Tris(hydroxymethyl)aminomethane
• 5-Amino-4,6-dichloropyrimidine
• 2,5-Diamino-4,6-dichloropyrimidine