Triethylamine → HCID 59258888, compound

HRID 472197Notes

Reaction equation

HRID 472197 reaction equation
[Br:1][C:2]1[C:15](=[O:16])[N:14]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:5]2[N:6]=[C:7](S(C)=O)[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.[NH2:22][CH2:23][C:24]([CH3:27])([OH:26])[CH3:25].C(N(CC)CC)C>O1CCOCC1.[Cl-].[Na+].O>[Br:1][C:2]1[C:15](=[O:16])[N:14]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:5]2[N:6]=[C:7]([NH:22][CH2:23][C:24]([OH:26])([CH3:27])[CH3:25])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 67236757HCID 67236757, compound

Product 1

HCID 59258888HCID 59258888, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-8-cyclopentyl-4-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one (600 mg, 1.62 mmol) and 1-amino-2-methylpropan-2-ol (294 mg, 2.34 mmol) in dioxane (6 mL) was added triethylamine (1.2 mL, 8.6 mmol). The mixture was then heated at 110° C. in a sealed tube for 1 h. The solution was poured into brine and extracted with ethyl acetate. The organic was dried (anhydrous sodium sulfate), filtered and concentrated to dryness. The crude product was purified by silica gel flash chromatography to give the title compound as a solid (565 mg, 88%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic was dried (anhydrous sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c1d049c1a79b4bbb8a9d9d4839021a96
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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