4-Fluorophenyl isothiocyanate → 3-(4-Fluorophenyl)-2-thioxo-2,3-dihydropyrido[3,2-d]pyrimidin-4(1H)-one

HRID 408830

Reaction equation

HRID 408830 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([O:10]CC)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[S:22])=[CH:16][CH:15]=1>N1C=CC=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:8](=[O:10])[C:3]3[N:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:21]2=[S:22])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 152414-Fluorophenyl isothiocyanateHCID 565054Ethyl 3-aminopyridine-2-carboxylate

Product 1

HCID 576141483-(4-Fluorophenyl)-2-thioxo-2,3-dihydropyrido[3,2-d]pyrimidin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of ethyl 3-aminopyridine-2-carboxylate (2.0 g, 12.0 mmol) and 4-fluorophenylisothiocyanate (1.84 g, 12.0 mmol) in 7 mL of anhydrous pyridine is stirred at 45° C. for 21 h. After cooling, the pyridine is evaporated in vacuo, and ice water is added to the residue. The resulting mixture is slurried in EtOAc and filtered to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.59 (1H, m), 7.79 (2H, m), 7.33 (4H, m).

Workup

  1. temperatureAfter cooling
  2. customthe pyridine is evaporated in vacuo, and ice water
  3. additionis added to the residue
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c5235bf44fe247beb342bde1ae6c455c
Source dataset
uspto-grants-2014_06
Patent number
US08759361B2

Linked notes

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