Ammonium Hydroxide → HCID 16123384, compound

HRID 2389957Notes

Reaction equation

HRID 2389957 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.[OH-].[NH4+:23]>O1CCOCC1>[NH2:23][C:7]1[N:8]=[C:9]([CH3:10])[C:4]2[CH:3]=[C:2]([Br:1])[C:15](=[O:16])[N:14]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 67236757HCID 67236757, compound

Product 1

HCID 16123384HCID 16123384, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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 (0.80 g, 2.16 mmol) in dioxane (5 mL) was added ammonium hydroxide (30%, 2.6 mL). The mixture was then heated at 110° C. in a sealed tube for 30 minutes. The solution was concentrated in vacuo and extracted with ethyl acetate (3×30 mL). The combined organics were washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered and concentrated to dryness to give the title compound as a brown crystalline solid (0.65 g, 93%).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organics were washed with saturated aqueous sodium chloride
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6ef9e5165b1f46e3810e659064549979
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

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