Tripropylamine → 4-Chloro-2-phenoxymethylquinazoline

HRID 1611616Notes

Reaction equation

HRID 1611616 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.C(N(CCC)CCC)CC.P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1

Participants

4

Reactant 3

HCID 7616TripropylamineHCID 24813Phosphorus oxychlorideHCID 178418749HCID 178418749, compound

Product 1

HCID 219910934-Chloro-2-phenoxymethylquinazoline

Conditions

Temperature
110 °C

Procedure

To a solution of 4-hydroxy-2-phenoxymethylquinazoline (2 g, 7.93 mmol) in phosphorus oxychloride (10 mL) is added tripropylamine (3.02 mL, 15.8 mmol) and the reaction mixture is heated for 30 minutes at 110° C. The excess phosphorus oxychloride is evaporated in vacuo, the residue is poured on ice cold aqueous NaHCO3 and extracted with ethyl acetate. The organic layer is washed with brine, dried, filtered and evaporated. The resulting residue is purified on flash chromatography (SiO2, hexane/AcOEt gradient) to give 4-chloro-2-phenoxymethylquinazoline.

Workup

  1. customThe excess phosphorus oxychloride is evaporated in vacuo
  2. additionthe residue is poured on ice cold aqueous NaHCO3
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting residue is purified on flash chromatography (SiO2, hexane/AcOEt gradient)

Sources & evidence

ORD record
ord-be6d6923256f4285a6210b06bdebc0ad
Source dataset
uspto-grants-2006_01
Patent number
US06989385B2

Reaction notes

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