Triethylamine → HCID 57860510, compound

HRID 1947150Notes

Reaction equation

HRID 1947150 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].Cl[C:37]1[CH:42]=[CH:41][N:40]=[CH:39][N:38]=1.C(N(CC)CC)C>CC(O)C.C(=O)([O-])O.[Na+]>[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:31][CH2:32][N:33]([C:37]2[CH:42]=[CH:41][N:40]=[CH:39][N:38]=2)[CH2:34][CH2:35]1)=[O:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6428344-ChloropyrimidineHCID 57860479HCID 57860479, compound

Product 1

HCID 57860510HCID 57860510, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of the compound of Example 77 (200 mg, 0.42 mmol), 4-chloropyrimidine (58 mg, 0.51 mmol) and triethylamine (0.12 mL, 0.85 mmol) in 2-propanol (4.0 mL) was heated under reflux for 23 hr. The reaction mixture was diluted with saturated sodium hydrogen carbonate solution, and extracted twice with a mixed solvent of ethyl acetate-methanol. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/methanol=0/100-5/95) and recrystallized from THF to give the title compound (97 mg, 42%) as a white solid.

Workup

  1. temperatureunder reflux for 23 hr
  2. extractionextracted twice with a mixed solvent of ethyl acetate-methanol
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/methanol=0/100-5/95)
  7. customrecrystallized from THF

Sources & evidence

ORD record
ord-6dce560168ae4d5eafe596e9d5e0b846
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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