Phosphorus oxychloride → HCID 86670031, compound

HRID 536061Notes

Reaction equation

HRID 536061 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[C:8]2[C:3]=1[C:4](=O)[N:5]=[CH:6][NH:7]2.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:4]1[C:3]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:2]=2[Cl:1])[N:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486914HCID 178486914, compound

Product 1

HCID 86670031HCID 86670031, compoundYield 65%

Conditions

Temperature
85 °C

Procedure

A mixture of 5-chloro-6,7-bis(methyloxy)-4(1H)-quinazolinone (100 mg, 0.42 mmol, prepared according to J. Med. Chem. (1999) 42 3860) in POCl3 (2 mL) was heated at 80-90° C. for 8 hours before being concentrated. The residue was treated with saturated aqueous NaHCO3 and extracted with EtOAc. The organic extract was dried (Na2SO4) and concentrated to give 4,5-dichloro-6,7-bis(methyloxy)quinazoline (70 mg, 65%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.94 (s, 1 H), 7.56 (s, 1 H), 4.05 (s, 3 H), 3.87 (s, 3 H). MS (m/z) 258.9 (M+H+).

Workup

  1. concentrationbefore being concentrated
  2. additionThe residue was treated with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-01d7a24e24f140dd8e885a05665eaa7e
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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