Triethylamine → 3-[(5-bromo-2-chloro-pyrimidin-4-yl)-(2-methylpropyl)amino]-N-methyl-propanamide

HRID 2234391Notes

Reaction equation

HRID 2234391 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][NH:11][C:12](=[O:20])[CH2:13][CH2:14][NH:15][CH2:16][CH:17]([CH3:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:3]([N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][CH2:13][C:12]([NH:11][CH3:10])=[O:20])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 61870051N-methyl-3-(2-methylpropylamino)propanamide2×

Product 1

HCID 866175693-[(5-bromo-2-chloro-pyrimidin-4-yl)-(2-methylpropyl)amino]-N-methyl-propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-2,4-dichloropyrimidine (Aldrich; 2.82 g, 12.37 mmol), N-methyl-3-(2-methylpropylamino)propanamide (Intermediate 86; 1.78 g; 11.25 mmol), Triethylamine (1.65 mL, 11.81 mmol) and DCM (40 mL) were combined and stirred over the weekend at room temperature. The reaction mixture was washed saturated aqueous sodium bicarbonate solution and gravity filtered through a PTFE cup and solvent evaporated. The residue was dissolved in DCM and passed through a silica column eluting with a gradient of 30-50% Ethyl Acetate/iso-hexane over 10 column volumes then 50% Ethyl Acetate/iso-hexane. Fractions containing product combined and evaporated to give the title compound as a white solid. (3.26 g, 83%)

Workup

  1. washThe reaction mixture was washed saturated aqueous sodium bicarbonate solution and gravity
  2. filtrationfiltered through a PTFE cup and solvent
  3. customevaporated
  4. dissolutionThe residue was dissolved in DCM
  5. washeluting with a gradient of 30-50% Ethyl Acetate/iso-hexane over 10 column volumes
  6. additionFractions containing product
  7. customevaporated

Sources & evidence

ORD record
ord-361d3adb2ea04f408e49169ee78efdd7
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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