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

HRID 2234400

Reaction equation

HRID 2234400 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][NH:12][CH2:13][CH2:14][C:15]([NH:17][CH3:18])=[O:16])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(N(CC)CC)C.[Br:26][C:27]1[C:28](Cl)=[N:29][C:30]([Cl:33])=[N:31][CH:32]=1>C(Cl)Cl>[Br:26][C:27]1[C:28]([N:12]([CH2:11][C:5]2[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:13][CH2:14][C:15]([NH:17][CH3:18])=[O:16])=[N:29][C:30]([Cl:33])=[N:31][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 618606733-[(3,5-dimethoxyphenyl)methylamino]-N-methyl-propanamide2×

Product 1

HCID 866175753-[(5-bromo-2-chloro-pyrimidin-4-yl)-[(3,5-dimethoxyphenyl)methyl]amino]-N-methyl-propanamideYield 26.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-[(3,5-dimethoxyphenyl)methylamino]-N-methyl-propanamide (Intermediate 98; 1 g, 3.96 mmol) was dissolved in DCM (10 mL) and triethylamine (0.68 mL, 4.36 mmol). 5-bromo-2,4-dichloropyrimidine (Aldrich; 993 mg, 4.36 mmol) was added and the mixture stirred at room temperature for 18 hours. The mixture was diluted with DCM and washed with water, brine, dried (MgSO4), filtered and evaporated to give a yellow gum which was purified on a 40 g ISCO companion eluting with 50-70% ethyl acetate in iso-hexane to give the title compound as a white solid (461 mg, 26%).

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give a yellow gum which
  6. customwas purified on a 40 g ISCO companion
  7. washeluting with 50-70% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-70422d208bb048c3a2c8d05054ed0ab8
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Linked notes

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