2,6-DIAMINO-4-METHOXY PYRIMIDINE Chemical Properties

Melting point:

162.0 to 166.0 °C

Boiling point:

429.4±48.0 °C(Predicted)

Density 

1.341±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

5.24±0.10(Predicted)

color 

White to Almost white

λmax

265nm(MeOH)(lit.)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

29335990

2,6-DIAMINO-4-METHOXY PYRIMIDINE Usage And Synthesis

Chemical Properties

Light yellow solid

Uses

2,4-Diamino-6-methoxypyrimidine is an organic amine compound used as a raw material for organic synthesis or as a pharmaceutical intermediate ingredient. The product can be used to prepare other heterocyclic compounds or anticancer active ingredients.

Synthesis

General procedure for the synthesis of 2,4-diamino-6-methoxypyrimidine from methanol and 2,4-diamino-6-chloropyrimidine: 9.2 g (0.40 mol) of sodium metal was added to a flask containing 320 mL of methanol and stirred until completely dissolved. Subsequently, 28.9 g (0.20 mol) of 2,4-diamino-6-chloropyrimidine was added to this solution. The reaction mixture was placed under reflux conditions and stirred continuously for 44 hours. Upon completion of the reaction, the precipitated sodium chloride was removed by filtration. The filtrate was concentrated to dryness to give the crude product. The crude product was dissolved in 300 mL of ethanol, heated to boiling and then thermally filtered. The filtrate was allowed to stand overnight to crystallize 2,4-diamino-6-methoxypyrimidine. The product can be further purified by recrystallization of the mother liquor. After drying, 2,4-diamino-6-methoxypyrimidine (58.8 g, 84% yield) was obtained as a white solid. Melting point: 166-169 °C. 1H-NMR (300 MHz, d6-DMSO): δ= 3.18 (s, 3H, 6-OMe), 5.06 (s, 1H, 5-H), 5.94 (s, 2H, NH2), 6.05 (s, 2H, NH2). 13C-NMR (125 MHz, d6-DMSO): δ= 52.8 ( 6-OMe), 76.1 (5-C), 163.3 (2-C), 166.3 (4-C), 170.8 (6-C).

References

[1] Organic and Biomolecular Chemistry, 2010, vol. 8, # 10, p. 2397 - 2407
[2] Patent: US2015/209257, 2015, A1. Location in patent: Paragraph 0239; 0240; 0241; 0242; 0243
[3] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 917 - 921

2,6-DIAMINO-4-METHOXY PYRIMIDINE(3270-97-1)Related Product Information

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• CHEMPACIFIC 39933
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• 2,4-DIAMINO-5-(NITRO)-6-(METHYLOXY)PYRIMIDINE
• 2-AMINO-6-(2,4-DICHLOROPHENOXY)PYRIMIDIN-4-YLAMINE
• 2-AMINO-4-METHOXY-6-MORPHOLIN-4-YLPYRIMIDINE-5-CARBALDEHYDE
• 2-AMINO-4-METHOXY-6-PYRROLIDIN-1-YLPYRIMIDINE-5-CARBALDEHYDE
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• N-[4-AMINO-5-NITROSO-6-(PENTYLOXY)PYRIMIDIN-2-YL]-N-METHYLAMINE
• N-(2-AMINO-6-METHOXY-5-NITROSOPYRIMIDIN-4-YL)THIOPHENE-2-CARBOXAMIDE
• 2,4-diamino-6-(benzyloxy)pyrimidine-5-carbonitrile
• 4-AMINO-2-(DIMETHYLAMINO)-5-(NITRO)-6-(METHYLOXY)PYRIMIDINE