4-Chloroquinazoline → Quinazoline

HRID 1798764Notes

Reaction equation

HRID 1798764 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C[O-].[Na+]>CO>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 788644-ChloroquinazolineHCID 10942334Sodium Methoxide

Product 1

HCID 9210QuinazolineYield 298.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the quinazoline 3 (0.14 g, 0.36 mmol) in MeOH (3 mL) was added NaOMe (1.44 mL, 0.72 mmol) at RT. The reaction was stirred overnight at RT. The reaction mixture was concentrated using rotavap (25° C.), then the residue was taken up with water (75 mL) and washed with EtOAc (3×50 mL). The aqueous phase was dried with lyophilizer to give final product 4 (0.14 g, 98% yield) as solid. LC/MS (10-99%) M/Z 406.0 retention time 3.32 min.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custom(25° C.)
  3. washwashed with EtOAc (3×50 mL)
  4. customThe aqueous phase was dried with lyophilizer

Sources & evidence

ORD record
ord-2ac502377aff4ed686be8038669c6137
Source dataset
uspto-grants-2013_01
Patent number
US08343980B2

Reaction notes

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