4-Chlorophenyl isothiocyanate → N-(4-chlorophenyl)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carbothioamide

HRID 631842Notes

Reaction equation

HRID 631842 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[F:11][C:12]1[C:13](=[NH:20])[N:14]([CH3:19])[C:15](=[O:18])[NH:16][CH:17]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:16]2[CH:17]=[C:12]([F:11])[C:13](=[NH:20])[N:14]([CH3:19])[C:15]2=[O:18])=[S:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 164804-Chlorophenyl isothiocyanateHCID 178481639HCID 178481639, compound

Product 1

HCID 75593364N-(4-chlorophenyl)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carbothioamideYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Chloro-4-isothiocyanatobenzene (78 mg, 0.46 mmol) was added to a stirred mixture of 5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one (60 mg, 0.42 mmol) and DMF (1.0 mL) and stirred at room temperature overnight. The solvent was removed and the residue was purified on normal phase chromatography (gradient, 0 to 10% MeOH-DCM). A second purification (gradient, 2 to 6% [10% NH4OH-MeOH]-DCM) gave the title compound as a yellow gum (68 mg, 52%); 1H NMR (400 MHz, DMSO-d6) δ 11.16 (s, 1H), 10.99 (s, 1H), 7.75 (d, J=39.7 Hz, 2H), 7.48-7.15 (m, 3H), 3.22 (d, J=13.8 Hz, 3H); 13C NMR (101 MHz, DMSO-d6) 6148.96, 144.90, 138.17, 136.27, 135.90, 128.51, 124.11, 123.07, 29.88; ESIMS m/z 311 ([M−H]+).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on normal phase chromatography (gradient, 0 to 10% MeOH-DCM)
  3. customA second purification (gradient, 2 to 6% [10% NH4OH-MeOH]-DCM)

Sources & evidence

ORD record
ord-15c95e963a404815a5b39870a5a30026
Source dataset
uspto-grants-2016_04
Patent number
US09321734B2

Reaction notes

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