Water → HCID 86585161, compound

HRID 982608Notes

Reaction equation

HRID 982608 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. Step 2 Preparation of 4-methylamino-2-methylthiopyrimidine-5-methanol

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-c0ea60e1768548da8a30b12d5eb6e1d3
Source dataset
uspto-grants-2005_03
Patent number
US06861423B2

Reaction notes

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