Water → HCID 86585161, compound

HRID 9763Notes

Reaction equation

HRID 9763 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[CH3:14][NH2:15].O>ClCCl.C(O)C>[CH3:14][NH:15][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 53249641Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate

Product 1

HCID 86585161HCID 86585161, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 20 g (86 mmol) of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (Aldrich Chemical Co., Milwaukee, Wis., USA) in 250 mL of dichloromethane was slowly added 35 mL (281 mmol) of a 33% solution of methylamine in ethanol. After stirring for 30 minutes, 150 mL of water was added and the phases were separated. The organic phase was dried over magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to give 19 g (97%) of ethyl 4-methylamino-2-methylthiopyrimidine-5-carboxylate as a white solid.

Workup

  1. customTo a 0° C.
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-21abd6ffa22b4380b8d9827c5a327a4a
Source dataset
uspto-grants-2006_08
Patent number
US07091347B2

Reaction notes

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