Toluene → 4-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

HRID 634755노트

반응식

HRID 634755 반응식
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.CN(C=O)C.C1(C)C=CC=CC=1.S(Cl)([Cl:38])=O>>[Cl:38][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

참가 물질

5

반응물 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1784867726-methoxy-7-(3-morpholin-4-ylpropoxy)-1H-quinazolin-4-one

생성물 1

HCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline수율 66%

실험 절차

A solution of 4-hydroxy-6-methoxy-7-(3-morpholinopropoxy)quinazoline (2.87 g, 9 mmol) and DMF (1 ml) in thionyl chloride (35 ml) was refluxed for 45 minutes. After addition of toluene, the volatiles were removed by evaporation. The residue was partitioned between ethyl acetate and water and the aqueous layer was adjusted to pH8 with 2M aqueous sodium hydroxide. The organic layer was washed with water and brine, dried (MgSO4) and the volatiles were removed by evaporation. The solid residue was purified by column chromatography eluting with a mixture of methylene chloride, acetonitrile and methanol (50/47.5/2.5) to give 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (2 g, 66%).

후처리

  1. customthe volatiles were removed by evaporation
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customthe volatiles were removed by evaporation
  6. customThe solid residue was purified by column chromatography
  7. washeluting with a mixture of methylene chloride, acetonitrile and methanol (50/47.5/2.5)

출처 및 근거

ORD 기록
ord-388f0d8624944a8a89f1c801f19366a8
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06184225B2

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