1,2-Dichloroethane → 4-Chloro-6,7-dimethoxyquinazoline

HRID 1784379ノート

反応式

HRID 1784379 の反応式
[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.C(NC(C)C)(C)C.[Cl:23]CCCl>>[Cl:23][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

参加物

4

反応物 3

HCID 111,2-DichloroethaneHCID 7912DiisopropylamineHCID 178486869HCID 178486869、化合物

生成物 1

HCID 27693644-Chloro-6,7-dimethoxyquinazoline収率 88.9%

反応条件

温度
80 °C

実験手順

To a suspension of 6,7-Dimethoxy-quinazolin-4-ol (1.65 g, 8.0 mmol) and phosporousoxychloride (1.52 ml, 16.4 mmol) in 1,2-dichloroethane (16 ml) was added diisopropylamine (3.48 ml, 20 mmol) in a dropwise fashion. The mixture was then heated to 80° C. under an inert atmosphere for 16 hours. After this time the reaction was cooled to room temperature and concentrated in vacuo to dryness, dissolved in CH2Cl2 (50 ml) and washed with sodium bicarbonate solution (5% aqueous, 2*25 ml). The organic layer was separated, dried using MgSO4, filtered and concentrated in vacuo to give a brown residue that was purified by flash chromatography (SiO2) eluted with CH2Cl2:EtOAc—2:98 then 5:95 to give the title compound (1.6 g, 88.9%) as a yellow solid. m/z (LC-MS, ESP): 207 [M+H]+, R/T=3.51 mins

後処理

  1. temperatureAfter this time the reaction was cooled to room temperature
  2. concentrationconcentrated in vacuo to dryness
  3. dissolutiondissolved in CH2Cl2 (50 ml)
  4. washwashed with sodium bicarbonate solution (5% aqueous, 2*25 ml)
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a brown residue that
  10. customwas purified by flash chromatography (SiO2)
  11. washeluted with CH2Cl2

出典と根拠

ORDレコード
ord-ee1961e04388462793459e5e4568c33e
出典データセット
uspto-grants-2009_03
特許番号
US07504397B2

反応ノート

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