Sodium Hydroxide → HCID 89782153, compound

HRID 1056364Notes

Reaction equation

HRID 1056364 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[N:8]([CH2:13][CH3:14])[C:7]2=[O:15].O=P(Cl)(Cl)[Cl:18].CCN(C(C)C)C(C)C.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:18])[N:8]([CH2:13][CH3:14])[C:7]2=[O:15]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 81531Diisopropylethylamine2×HCID 89783700HCID 89783700, compound

Product 1

HCID 89782153HCID 89782153, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8-bromo-3-ethylquinazoline-2,4(1H,3H)-dione (736 mg, 2.74 mmol, 481b), POCl3 (1.5 mL, 16.42 mmol, Sigma Aldrich), and DIPEA (0.9 mL, 5.47 mmol) was heated to reflux. Additional DIPEA (0.9 mL, 5.47 mmol) was added. It was stirred overnight at reflux. The mixture was cooled to RT and poured into rapidly stirred water at 0° C. It was basified to pH 10 with 10 N NaOH (aq.) to give an orange solution. The solution was extracted with DCM, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a yellow orange solid (398 mg, 57%). m/z (ESI, +ve) 286.9 (M+H)+.

Workup

  1. temperaturewas heated to reflux
  2. temperatureat reflux
  3. customto give an orange solution
  4. extractionThe solution was extracted with DCM
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73d5c76dbf5d4822b4a6c94ffcf3557b
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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