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

HRID 2234388Notes

Reaction equation

HRID 2234388 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH2:10]([NH:12][CH2:13][CH2:14][C:15]([NH:17][CH3:18])=[O:16])[CH3:11].C(N(CC)CC)C>C(#N)C>[Br:1][C:2]1[C:3]([N:12]([CH2:10][CH3:11])[CH2:13][CH2:14][C:15]([NH:17][CH3:18])=[O:16])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 618617253-(ethylamino)-N-methylpropanamide2×

Product 1

HCID 866175683-[(5-bromo-2-chloro-pyrimidin-4-yl)-ethyl-amino]-N-methyl-propanamideYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-2,4-dichloropyrimidine (Aldrich; 1.14 g, 5.00 mmol), 3-ethylamino-N-methyl-propanamide (Intermediate 83; 0.642 g, 5.00 mmol) and triethylamine (0.71 mL, 5.10 mmol) were combined in acetonitrile (25 mL) and heated to 100° C. for 4 hrs. The solvent was removed under reduced pressure and the residue taken up in Ethyl Acetate, washed with water and purified by flash silica chromatography (companion, 40 g, 0-10% Methanol/DCM) to give the title compound as a white solid (1.06 g, 3.3 mmol, 66%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with water
  3. custompurified by flash silica chromatography (companion, 40 g, 0-10% Methanol/DCM)

Sources & evidence

ORD record
ord-c1523ba3cc0c4de68ecd83b37e52922f
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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