Triethylamine → 4-Chloro-6,7-dimethoxyquinazoline

HRID 351410Notes

Reaction equation

HRID 351410 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2O.P(Cl)(Cl)([Cl:18])=O.C(N(CC)CC)C>C(Cl)Cl>[Cl:18][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178486869HCID 178486869, compound

Product 1

HCID 27693644-Chloro-6,7-dimethoxyquinazolineYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6,7-Dimethoxy-quinazolin-4-ol (1.00 g, 4.85 mmol, 1 eq.), phosphorous oxychloride (4.07 mL, 43.6 mmol, 9.00 eq.) and triethylamine (6.08 mL, 43.6 mmol, 9 eq.) were refluxed for 2 hours. Stripped then restripped 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 to 3:1 Hexanes/EtOAc. Obtained 0.84 g of off-white solids as product. LCMS detects (M+H)+=225.

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 to 3:1 Hexanes/EtOAc

Sources & evidence

ORD record
ord-aeb449ca2ab848db9caf05645d2160d3
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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