2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER Chemical Properties

Melting point:

147-149℃

Boiling point:

349℃

Density 

1.261

Flash point:

165℃

storage temp. 

2-8°C(protect from light)

pka

1.94±0.10(Predicted)

Appearance

White to light yellow Solid

Safety Information

HS Code 

2933599590

2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER Usage And Synthesis

Uses

2-Amino-pyrimidine-5-carboxylic Acid Ethyl Ester is a reagent used in the synthesis of retinoidal pyrimidinecarboxylic acids.

Synthesis

The general procedure for the synthesis of ethyl 2-aminopyrimidine-5-carboxylate from ethyl 2-methylsulfonyl-5-pyrimidinecarboxylate was as follows: ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (2.15 g, 9.34 mmol) was dissolved in acetonitrile (11.7 mL) and stirred at room temperature. Subsequently, 32% aqueous ammonium hydroxide solution (11.36 mL, 93 mmol) was added slowly and dropwise. The reaction mixture transformed into a white suspension within seconds. The acetonitrile was removed by rotary evaporator and the remaining aqueous phase suspension was filtered through a Brinell funnel. The resulting solid was washed with distilled water (20 mL) and dried to give ethyl 2-aminopyrimidine-5-carboxylate as a white solid (1.192 g, 7.13 mmol, 76% yield, MS/ESI+ 168.1 [MH]+).

References

[1] Patent: US2013/79313, 2013, A1. Location in patent: Paragraph 1024
[2] Patent: WO2013/45280, 2013, A1. Location in patent: Page/Page column 276

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