Methyl iodide → 4-Methyl-5-(2-(methylthio)pyrimidin-4-yl)thiazol-2-amine

HRID 444891Notes

Reaction equation

HRID 444891 reaction equation
[OH-].[Na+].CN(C)C=[CH:6][C:7]([C:9]1[S:13][C:12]([N:14]=[CH:15]N(C)C)=[N:11][C:10]=1[CH3:19])=O.[NH2:21][C:22]([NH2:24])=[S:23].[CH3:25]I>C(O)C.O>[CH3:6][C:7]1[N:21]=[C:22]([NH2:24])[S:23][C:9]=1[C:10]1[CH:19]=[CH:15][N:14]=[C:12]([S:13][CH3:25])[N:11]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 67218485N'-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine

Product 1

HCID 575066564-Methyl-5-(2-(methylthio)pyrimidin-4-yl)thiazol-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Powdered sodium hydroxide (1.09 g) is added to a solution of N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine (2.0 g, prepared as described by S. Wang et al J. Med. Chem. 2004, 47, 1662-1675.) and thiourea (0.57 g) in ethanol (25 ml) and the mixture is heated at reflux for 3 hour with stirring. The reaction mixture is cooled to room temperature and water then methyliodide (0.47 ml) is added. After 1 hour at room temperature the ethanol is removed by evaporation and water is added and the pH is adjusted to 7 with 2N aqueous hydrochloric acid. The title compound is then obtained by filtration. ESI-MS: M+H 239 and M−H 237.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 3 hour
  3. customAfter 1 hour at room temperature the ethanol is removed by evaporation and water
  4. additionis added

Sources & evidence

ORD record
ord-49798f1470f04921a328df002dbb719d
Source dataset
uspto-grants-2013_07
Patent number
US08476268B2

Reaction notes

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