Triethylamine → 4,6-Dichloro-2-propylquinazoline

HRID 1391907Notes

Reaction equation

HRID 1391907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[N:6]=[C:5]2O.P(Cl)(Cl)([Cl:18])=O.C(N(CC)CC)C>C(Cl)Cl>[Cl:18][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178440201HCID 178440201, compound

Product 1

HCID 210882734,6-Dichloro-2-propylquinazolineYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Chloro-2-propyl-quinazolin-4-ol (810 mg, 3.64 mmol, 1 eq.), phosphorous oxychloride (3.30 mL, 35.1 mmol, 9.64 eq.) and triethylamine (1.63 mL, 11.7 mmol, 3.21 eq.) were refluxed for 2 hours. Stripped 3× from methylene chloride then dissolved in methylene chloride and rinsed 3× with saturated sodium bicarbonate, 1× with brine. Dried and stripped in vacuo to give an amber oil. Purified over silica gel in 9:1 Hexanes/EtOAc. Obtained 510 mg of off-white solids as product. The product was used immediately in Example 121 Part D.

Workup

  1. washrinsed 3× with saturated sodium bicarbonate, 1× with brine
  2. customDried
  3. customto give an amber oil
  4. customPurified over silica gel in 9:1 Hexanes/EtOAc

Sources & evidence

ORD record
ord-176be9ada4934fde9f073bec2e94b18f
Source dataset
uspto-grants-2008_03
Patent number
US07338947B2

Reaction notes

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