Methylamine → 4-(Methylamino)-2-(methylthio)pyrimidine-5-carbonitrile

HRID 1783507Notes

Reaction equation

HRID 1783507 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[CH3:12][NH2:13]>C(OCC)C>[CH3:12][NH:13][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Product 1

HCID 106789344-(Methylamino)-2-(methylthio)pyrimidine-5-carbonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Through a 5° C. solution of 14.5 g (78.1 mmol) of 4-chloro-2-(methylthio)-5-pyrimidinecarbonitrile in 800 mL of diethyl ether is bubbled methylamine gas for a period of 15 minutes. The reaction mixture is allowed to warm to room temperature, set overnight, and filtered. The solids are washed with diethyl ether, then efficiently with 50 mL of water, and dried to give 12.0 g (81%) of the title compound: mp 189-190° C.

Workup

  1. filtrationfiltered
  2. washThe solids are washed with diethyl ether
  3. dry with materialefficiently with 50 mL of water, and dried

Sources & evidence

ORD record
ord-55f2d7808cfe4103af4db6dfb4d082d3
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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