Dimethylamine → HCID 4190857, compound

HRID 1044661Notes

Reaction equation

HRID 1044661 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH:11]([N:14](C(C)C)[CH2:15]C)(C)C.CNC.O>O1CCCC1>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([N:14]([CH3:15])[CH3:11])[CH:7]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 4190857HCID 4190857, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-dichloro-2-methylmercaptopyrimidine (10.0 g, 51 mmol) and diisopropyl ethylamine (17.5 ml, 102 mmol) was dissolved in tetrahydrofuran (400 ml), and a 50% aqueous dimethylamine solution (7.6 ml, 84 mmol) was dripped over the course of 1 hour into this solution under ice cooling. After this mixture liquid was agitated overnight at room temperature, water was added and extraction was carried out 2 times with ethyl acetate. After washing the organic layer with saturated saline, drying was done with MgSO4, the solvent was distilled away under reduced pressure, and 6-chloro-4-dimethylamino-2-methylmercaptopyrimidine was obtained. This was used for the next reaction without separation or refinement. Morpholine (100 ml) was added to this, and it was agitated overnight at 100 degrees Celsius. After allowing to cool, water was added and extraction was carried out 2 times with dichloromethane. After washing the organic layer with saturated saline, drying was done with MgSO4, the solvent was distilled away under reduced pressure. The residue was washed with ether and 11.3 g of coarse crystals of 4-dimethylamino-2-methylsulfanyl-6-morpholinopyrimidine was obtained (2 step yield: 87%).

Workup

  1. customwas dripped over the course of 1 hour into this solution under ice cooling
  2. extractionextraction
  3. washAfter washing the organic layer with saturated saline
  4. customdrying
  5. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-142ccab2e5cd49dabb7a7b2d9c20c7e2
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

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