Ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylate → Ethyl 6-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)-1,6-dihydropyrimidine-5-carboxylate

HRID 626457

Reaction equation

HRID 626457 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][NH2:7].CS[C:10]1[NH:11][C:12](=[O:21])[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:15]=1>CO>[O:21]=[C:12]1[NH:11][C:10]([NH:7][CH2:6][CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)=[N:15][CH:14]=[C:13]1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 239049Ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylateHCID 253298Tetrahydrofurfurylamine

Product 1

HCID 17229209Ethyl 6-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)-1,6-dihydropyrimidine-5-carboxylateYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(tetrahydrofuran-2-yl)methanamine (142 mg, 1.40 mmol) was added into ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrmidine-5-carboxylate (300 mg, 1.40 mmol) in methanol and refluxed overnight. After half of the starting material was consumed, the reaction mixture was reheated again overnight. Then the reaction mixture was cooled and the precipitate filtered. 1H-NMR confirmed the product as ethyl 6-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)-1,6-dihydropyrimidine-5-carboxylate (HGN-0017) (176 mg, 47% yield).

Workup

  1. temperaturerefluxed overnight
  2. customAfter half of the starting material was consumed
  3. temperatureThen the reaction mixture was cooled
  4. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-48636987876e47b1832aee1079518157
Source dataset
uspto-grants-2016_04
Patent number
US09309232B2

Linked notes

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