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ChemicalBook CAS DataBase List Ethyl 2-(4-(hydroxymethyl)piperidin-1-yl)pyrimidine-5-carboxylate

Ethyl 2-(4-(hydroxymethyl)piperidin-1-yl)pyrimidine-5-carboxylate synthesis

8synthesis methods
-

Yield:875318-46-0 99%

Reaction Conditions:

Stage #1: 4-piperidinemethanolwith potassium carbonate in N,N-dimethyl-formamide;acetonitrile at 20; for 0.166667 h;
Stage #2: ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate in N,N-dimethyl-formamide;acetonitrile; for 0.333333 h;

Steps:

3.1

Stage 1 - Coupling; Piperidin-4yl-methanol (2.48g, 21.55mmol) was stirred in 1 :1 DMF/MeCN (2OmL) with K2CO3 (8.9g, 64.65mmol) for 10 minutes at RT under a nitrogen atmosphere. Intermediate F (5g, 21.55mmol) was then added and the reaction allowed to stir for 20 minutes. It was then diluted with H2O (10OmL) and extracted with EtOAc (2 x 10OmL). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to give the product as an orange solid which was used in the next step without further purification (5.7Og, 99%). m/z = 266 [M+H]+.

References:

WO2008/53131,2008,A1 Location in patent:Page/Page column 51; 53