Triethylamine → HCID 22632982, compound

HRID 2270258Notes

Reaction equation

HRID 2270258 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([O:13][N:14]1[C:19](=[O:20])[C:18]2[CH:21]=[C:22]([F:26])[C:23](Cl)=[N:24][C:17]=2[N:16]([CH2:27][CH2:28][CH2:29][CH3:30])[C:15]1=[O:31])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(#N)C>[CH2:6]([O:13][N:14]1[C:19](=[O:20])[C:18]2[CH:21]=[C:22]([F:26])[C:23]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:24][C:17]=2[N:16]([CH2:27][CH2:28][CH2:29][CH3:30])[C:15]1=[O:31])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 22632873HCID 22632873, compound

Product 1

HCID 22632982HCID 22632982, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyrrolidine (0.04 mL, 0.52 mmol) was added to a solution of 3-benzyloxy-1-butyl-7-chloro-6-fluoro-1H-pyrido[2,3-d]pyrimidine-2,4-dione (Example O-2, 0.16 g, 0.42 mmol) and triethylamine (0.36 mL, 2.6 mmol) in 20 mL of acetonitrile. The solution was warmed to reflux for 17 hours, cooled, and concentrated to a solid. The solid was dissolved in chloroform washed with 1N HCl, saturated NaHCO3, brine, and dried over magnesium sulfate. The solution was concentrated to give 0.14 g of the title compound as a solid

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux for 17 hours
  3. temperaturecooled
  4. concentrationconcentrated to a solid
  5. dissolutionThe solid was dissolved in chloroform
  6. washwashed with 1N HCl, saturated NaHCO3, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-9803db6c6c174cfcaa4ed613e60b7e32
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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