2-Methyl-3-butyn-2-ol → 4-(Methylthio)-7-(3-hydroxy-3-methylbut-1-ynyl)quinazoline

HRID 2233265노트

반응식

HRID 2233265 반응식
[CH3:1][S:2][C:3]1[C:12]2[C:7](=[CH:8][C:9](OS(C(F)(F)F)(=O)=O)=[CH:10][CH:11]=2)[N:6]=[CH:5][N:4]=1.[CH3:21][C:22]([OH:26])([C:24]#[CH:25])[CH3:23].C(N(CC)CC)C>CN(C)C=O.[Cu]I>[CH3:1][S:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:25]#[C:24][C:22]([OH:26])([CH3:23])[CH3:21])=[CH:10][CH:11]=2)[N:6]=[CH:5][N:4]=1

참가 물질

6

반응물 3

HCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 857840454-(Methylthio)-7-(trifluoromethanesulphonyloxy)quinazoline

생성물 1

HCID 686768364-(Methylthio)-7-(3-hydroxy-3-methylbut-1-ynyl)quinazoline수율 174.2%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

4-(Methylthio)-7-(trifluoromethanesulphonyloxy)quinazoline (592 mg, 1.82 mmol) in dimethylformamide (20 ml) was reacted with 2-methyl-3-butyn-2-ol (0.53 ml, 0.54 mmol) in the presence of bis dichloro(triphenylphosphine)palladium (64 mg, 0.091 mmol), copper (I) iodide (20 mg) and triethylamine (1.1 ml, 0.8 mmol), at 90° C. for 2.5 hours. The solvent was removed in vacuo, aqueous hydrochloric acid (2N) was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and the solvents were evaporated in vacuo. Purification by flash chromatography on silica gel, eluting with isohexane/ethyl acetate (55:45), yielded, 4-(methylthio)-7-(3-hydroxy-3-methylbut-1-ynyl)quinazoline (243 mg, 51% yield):

후처리

  1. customThe solvent was removed in vacuo, aqueous hydrochloric acid (2N)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customthe solvents were evaporated in vacuo
  7. customPurification by flash chromatography on silica gel
  8. washeluting with isohexane/ethyl acetate (55:45)
  9. customyielded

출처 및 근거

ORD 기록
ord-c25752486bd542dcbe529de59fcf65e2
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709479B1

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