4-(4-MethoxybenzylaMino)-5-ethoxycarbonyl-2-MethylthiopyriMidine Chemical Properties

Boiling point:

493.6±35.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

2.81±0.10(Predicted)

Appearance

White to off-white Solid

4-(4-MethoxybenzylaMino)-5-ethoxycarbonyl-2-MethylthiopyriMidine Usage And Synthesis

Uses

4-(4-Methoxybenzylamino)-2-methanethiopyrimidine-5-carboxylic Acid Ethyl Ester is used in the preparation of pyrimidine derivatives for the treatment of metabolic bone disease.

Synthesis

Example 14: Synthesis of ethyl 4-[[(4-methoxyphenyl)methyl]amino]-2-methylthio-5-pyrimidinecarboxylate To a 60 mL solution of tetrahydrofuran containing ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (6.05 g, 26.07 mmol) was sequentially added triethylamine (11 mL, 79.5 mmol) and 4-methoxybenzylamine (3.6 mL, 27.6 mmol) at room temperature. The reaction mixture was stirred for 1 h. The reaction solution was filtered and the resulting white solid was washed with ethyl acetate. The filtrate and washings were combined and concentrated under reduced pressure. The residue was partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give ethyl 4-[[(4-methoxyphenyl)methyl]amino]-2-methylthio-5-pyrimidinecarboxylate (7.60 g, 88% yield) with a melting point of 72-74 °C. Elemental analysis: C16H19N3O3S Calculated values: c, 57.64; h, 5.74; n, 12.60. Measured values: C, 57.65; H, 5.80; N, 12.57.

References

[1] Patent: US2004/224958, 2004, A1
[2] Patent: US6498163, 2002, B1
[3] Patent: WO2015/92431, 2015, A1. Location in patent: Page/Page column 94; 95

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