Dimethylamine → HCID 58504442, compound

HRID 2367524Notes

Reaction equation

HRID 2367524 reaction equation
CS(O[CH2:6][C@H:7]1[O:12][CH2:11][C@@H:10]([CH3:13])[N:9]([C:14]2[CH:19]=[C:18]([Cl:20])[N:17]=[C:16]([NH:21][CH3:22])[N:15]=2)[CH2:8]1)(=O)=O.[CH3:23][NH:24][CH3:25].C([O-])(O)=O.[Na+]>O>[Cl:20][C:18]1[CH:19]=[C:14]([N:9]2[C@H:10]([CH3:13])[CH2:11][O:12][C@H:7]([CH2:6][N:24]([CH3:25])[CH3:23])[CH2:8]2)[N:15]=[C:16]([NH:21][CH3:22])[N:17]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 58504570HCID 58504570, compound

Product 1

HCID 58504442HCID 58504442, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of {(2S,5R)-4-[6-chloro-2-(methylamino)-4-pyrimidinyl]-5-methyl-2-morpholinyl}methyl methanesulfonate (161 mg, 0.46 mmol) and dimethylamine (2.0 M in THF, 5.0 mL, 10.0 mmol) was stirred at 120° C. in a sealed tube for 32 hours. The mixture was cooled, poured into saturated aqueous NaHCO3 (15 mL), diluted with water (5 mL), and extracted with EtOAc (3×15 mL). The extracts were washed with brine (15 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (24 g SiO2, CH2Cl2 to 95/5/0.5 CH2Cl2/CH3OH/NH4OH gradient) to give the title compound (62 mg, about 85% purity) as an off-white foam. LC-MS (ES) m/z=300, 302 [M+H]+.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (3×15 mL)
  3. washThe extracts were washed with brine (15 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (24 g SiO2, CH2Cl2 to 95/5/0.5 CH2Cl2/CH3OH/NH4OH gradient)

Sources & evidence

ORD record
ord-9716a3e97f4f47398649cba65b63940b
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…