Dimethyl Sulfoxide → HCID 131733249, compound

HRID 509448Notes

Reaction equation

HRID 509448 reaction equation
[ClH:1].[NH2:2][C:3]1[C:8]([CH2:9][Cl:10])=[CH:7][N:6]=[C:5]([CH2:11]C)[N:4]=1.[F:13][CH2:14][CH2:15][C:16]1[S:20][CH:19]=[N:18][C:17]=1[CH3:21].CS(C)=O>C(O)(C)C>[ClH:10].[Cl-:1].[NH2:2][C:3]1[C:8]([CH2:9][N:18]2[C:17]([CH3:21])=[C:16]([CH2:15][CH2:14][F:13])[S:20][CH2:19]2)=[CH:7][N:6]=[C:5]([CH3:11])[N:4]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 20323417HCID 20323417, compoundHCID 118060526HCID 118060526, compound

Product 1

HCID 131733249HCID 131733249, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To 25 ml flask 1.7 g (8.2 mmol) of 4-amino-5-chloromethyl 2-ethylpyrimidine hydrochloride and 1.3 g (9.0 mmol) of 5-(2-fluoroethyl)-4-methylthiazole were charged, followed by 1 ml of DMSO. The reaction mixture was stirred at 100° C. for 20 minutes. Then it was cooled to room temperature and 10 ml of isopropanol was added. After standing for 2 h, a precipitate was formed and filtered. 2 g of 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-fluoroethyl)-4-methylthiazol chloride hydrochloride was obtained as white solid (yield 70%).

Workup

  1. temperatureThen it was cooled to room temperature
  2. waitAfter standing for 2 h
  3. customa precipitate was formed
  4. filtrationfiltered

Sources & evidence

ORD record
ord-924622f8267f46679391a704f8a3cfdc
Source dataset
uspto-grants-2015_08
Patent number
US09096581B2

Reaction notes

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