Benzylamine → N-benzyl-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxamide

HRID 645520Notes

Reaction equation

HRID 645520 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.C(N(CC)CC)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.CCOC(C)=O.O>[CH2:21]([NH:28][C:8]([C:7]1[C:6]([Cl:11])=[N:5][C:4]([S:12][CH3:13])=[N:3][C:2]=1[Cl:1])=[O:9])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 726991444,6-Dichloro-2-(methylthio)pyrimidine-5-carbonyl chloride

Product 1

HCID 86627801N-benzyl-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,6-dichloro-2-methylsulfanylpyrimidine-5-carbonyl chloride in THF (15 mL), triethylamine (2.3 mmol) and benzylamine (2.5 mmol) are added at 0° C. After stirred at room temperature for 2 h, the reaction mixture is diluted with AcOEt and H2O. The mixture is extracted twice with AcOEt. The organic layer is dried over Na2SO4, filtered, and concentrated. The residue is purified by silica gel column chromatography to give 4,6-dichloro-2-methylsulfanylpyrimidine-5-carboxylic acid benzylamide as a white solid. 1H-NMR (CDCl3), δ 2.57 (3H, s), 4.66 (2H, d), 6.08 (1H, br s), 7.31-7.35 (2H, m), 7.36-7.38 (3H, m).

Workup

  1. extractionThe mixture is extracted twice with AcOEt
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3db8fb840033460fa295ad251a5fb9de
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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