Phosphorus oxychloride → HCID 86683183, compound

HRID 1852083Notes

Reaction equation

HRID 1852083 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11](O)[C:10]2[C:5](=[CH:6][C:7]([O:14][CH3:15])=[CH:8][CH:9]=2)[N:4]=1.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:11]1[C:10]2[C:5](=[CH:6][C:7]([O:14][CH3:15])=[CH:8][CH:9]=2)[N:4]=[C:3]([O:2][CH3:1])[N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178487767HCID 178487767, compound

Product 1

HCID 86683183HCID 86683183, compoundYield 36.1%

Procedure

A solution of 2,7-dimethoxyquinazolin-4-ol (155 mg, 0.752 mmol) in POCl3 (2 ml, 21.46 mmol) was refluxed for 4 h. The reaction mixture was concentrated. The residue was dissolved in DCM and the pH was adjusted to 7 with 4N NaOH. The organic phase was collected and dried over sodium sulfate, filtered, then concentrated under vacuum. The crude material was purified by silica gel chromatography using 50% DCM in hexanes. The product fractions were collected and the solvent removed under vacuum to give 4-chloro-2,7-dimethoxyquinazoline (61 mg, 36% yield). MS: MS m/z 225.1 (M++1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in DCM
  3. customThe organic phase was collected
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude material was purified by silica gel chromatography
  8. customThe product fractions were collected
  9. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-62646a28d47146ccbed4a3e5f1f7586f
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

Loading…