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

HRID 2233265ノート

反応式

HRID 2233265 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

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):

後処理

  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

出典と根拠

ORDレコード
ord-c25752486bd542dcbe529de59fcf65e2
出典データセット
uspto-grants-2010_05
特許番号
US07709479B1

反応ノート

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