2-Bromoethanol → HCID 38916047, compound

HRID 517099Notes

Reaction equation

HRID 517099 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:12].Br[CH2:14][CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([CH2:14][CH2:15][OH:16])[C:5]2=[O:12]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 1354449056-bromoquinazolin-4-ol

Product 1

HCID 38916047HCID 38916047, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

6-Bromoquinazolin-4(3H)-one Compound 178-A (1.0 g), 2-bromoethanol (1.1 g), and potassium carbonate (610 mg) were heated in DMA (10 mL) at 80° C. for 16 h. Reaction was extracted with water and dichloromethane (3 times), combined organic layers washed with brine, over sodium sulphate and concentrated. Residue was triturated with acetonitrile to yield 6-bromo-3-(2-hydroxyethyl)quinazolin-4(3H)-one Compound 178-B (810 mg) as a white solid. MS m/z (ESI)=268.9 (base peak, 79Br−M+H+); 270.9 (81Br−M+H+); 290.9 (79Br−M+Na+); 292.9 (81Br−M+Na+).

Workup

  1. customReaction
  2. extractionwas extracted with water and dichloromethane (3 times)
  3. washwashed with brine, over sodium sulphate
  4. concentrationconcentrated
  5. customResidue was triturated with acetonitrile

Sources & evidence

ORD record
ord-79133212efb043f28296d2bcf4d777fa
Source dataset
uspto-grants-2015_08
Patent number
US09115096B2

Reaction notes

Loading…