Dimethylamine → HCID 85945614, compound

HRID 1455008Notes

Reaction equation

HRID 1455008 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](Cl)=[O:10])=[C:4]([Cl:12])[N:3]=1.C(=O)(O)[O-].[Na+].[CH3:18][NH:19][CH3:20]>C(Cl)Cl.O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([N:19]([CH3:20])[CH3:18])=[O:10])=[C:4]([Cl:12])[N:3]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 132643612,4,6-Trichloropyrimidine-5-carbonyl chloride

Product 1

HCID 85945614HCID 85945614, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the subtitle product of step ii) (2.0 g) in DCM (20 ml) and sodium bicarbonate (1.36 g) in water (20 ml) at 0° C. was added dimethylamine (1.00 ml, 40% aqueous) dropwise. The reaction mixture was stirred at room temperature for 2 h before DCM (40 ml) was added and the aqueous layer separated. The organic layer was washed with water (20 ml), brine (10 ml) and dried (MgSO4). The solid was filtered and the solvent evaporated to dryness under reduced pressure. The residue was purified by column chromatography (EtOAc/isohexane (1:1)) to yield the subtitle compound as an off white solid. Yield 1.9 g

Workup

  1. additionwas added
  2. customthe aqueous layer separated
  3. washThe organic layer was washed with water (20 ml), brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationThe solid was filtered
  6. customthe solvent evaporated to dryness under reduced pressure
  7. customThe residue was purified by column chromatography (EtOAc/isohexane (1:1))

Sources & evidence

ORD record
ord-06b5000d3d9843c4bcd11a028cee8356
Source dataset
uspto-grants-2009_01
Patent number
US07482355B2

Reaction notes

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