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

HRID 1784379노트

반응식

HRID 1784379 반응식
[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

참가 물질

4

반응물 3

HCID 111,2-DichloroethaneHCID 7912DiisopropylamineHCID 178486869HCID 178486869, 화합물

생성물 1

HCID 27693644-Chloro-6,7-dimethoxyquinazoline수율 88.9%

반응 조건

온도
80 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-ee1961e04388462793459e5e4568c33e
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504397B2

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