ChemicalBook CAS DataBase List Methyl 4-(4-Fluorophenyl)-6-isopropyl-2-(methylthio)pyrimidine-5-carboxylate

Methyl 4-(4-Fluorophenyl)-6-isopropyl-2-(methylthio)pyrimidine-5-carboxylate synthesis

7synthesis methods

Product Name:Methyl 4-(4-Fluorophenyl)-6-isopropyl-2-(methylthio)pyrimidine-5-carboxylate
CAS Number:160009-35-8
Molecular formula:C16H17FN2O2S
Molecular Weight:320.38

885100-76-5 Synthesis

Methyl 6-(4-Fluorophenyl)-4-isopropyl-2-methylthio-1,4-dihydropyrimidine
-5-carboxylate

885100-76-5
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Methyl 4-(4-Fluorophenyl)-6-isopropyl-2-(methylthio)pyrimidine-5-carboxylate

160009-35-8
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$140.00/25mg

Yield:160009-35-8 52.12%

Reaction Conditions:

with chloranil in toluene at 65 - 70; for 5 h;

Steps:

4

Example-4; Preparation of Methyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylthio) pyrimidine-5-carboxylate; In a round bottom flask equipped with stirrer, hot plate, water bath, condenser , thermometer, Charge toluene (249 ml) at 25 to 35 ⁰C. Add p-Chloranil (42g, 0.1708 mol). Raise the temperature to 65 ⁰C to 70 ⁰C. Add Methyl 6-(4-fluorophenyl)-4-isopropyl-2- (methylthio)-l,4-dihydiOpyiimidine-5-carboxylate (205.25 g toluene solution) & 70 ml toluene at 65 to 70 ⁰C over a period of 1 hour. Stir the mass at 65 to 70 ⁰C for 4 hours. Check TLC for the completion of the reaction. Filter the contents at room temperature. Wash the wet cake with 42 ml of toluene. Add the filtrate (560 ml) into the flask at room temperature. Wash this organic layer twice with 2% aqueous NaOH solution (394 ml demineralized water + 7.88 gm NaOH) at 25 to 35⁰C. Add organic layer into R.B. Flask. Wash this organic layer twice with (280 ml) of demineralized water at 25 to 35⁰C. Diy organic layer using anhydrous sodium sulfate. Distill toluene under vacuum at 50-55⁰C. Add (30 ml) of isopropyl alcohol into the flask. Raise the temperature & Stir the contents at 75 to 8O⁰C for 15 minutes. Then cool to 25 to 35 ⁰C. Again stir and cool to 0 to 2⁰C & stir for 1 hour. Filter the contents. Wash the cake twice with (10 ml) chilled Isopropyl alcohol. Dry the material at 55 to 60 ⁰C. Yield = 25.88- 27.0 gm.; %Yield = 52.12 - 54.38 %Purity by HPLC= 97.46 %Assay= 97.44 %