Phosphorus oxychloride → 7-benzyloxy-4-chloro-2-methyl-quinazoline

HRID 1271214Notes

Reaction equation

HRID 1271214 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[N:14]=[C:15]([CH3:19])[NH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:23]>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:23])=[N:14][C:15]([CH3:19])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178433411HCID 178433411, compound

Product 1

HCID 115074897-benzyloxy-4-chloro-2-methyl-quinazolineYield 47.2%

Procedure

A suspension of 0.9 g (3.38 mmol) of 7-benzyloxy-2-methyl-1H-quinazolin-4-one in POCl3 (4.6 ml, 50 mmol) were heated at reflux for 1.5 h. The reaction mixture was then concentrated in vacuo, the residue was partitioned between CH2Cl2 and cold diluted NaHCO3 (pH 7–8). The layers were separated and the aqueous layer twice extracted with CH2Cl2. The combined organic layers washed with saturated NaHCO3, brine and then dried over Mg2SO4. The solvent was removed in vacuo give 0.45 g (47.2%) of crude 7-benzyloxy-4-chloro-2-methyl-quinazoline as a dark red waxy solid which was used directly in the next step without further purification. Rf: 0.9 (CH2Cl2/MeOH: 9/1; starting material with Rf: 0.7).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 1.5 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customthe residue was partitioned between CH2Cl2 and cold diluted NaHCO3 (pH 7–8)
  5. customThe layers were separated
  6. extractionthe aqueous layer twice extracted with CH2Cl2
  7. washThe combined organic layers washed with saturated NaHCO3, brine
  8. dry with materialdried over Mg2SO4
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8066629e7da04d4aa9d9ad2fa9c9fa21
Source dataset
uspto-grants-2007_04
Patent number
US07205309B2

Reaction notes

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