5-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine → 5-(2,8-Dimethyl-5h-dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedione

HRID 1275887

反応式

HRID 1275887 の反応式
C([Li])CCC.Br[C:7]1[C:8]([O:18]C(C)(C)C)=[N:9][C:10]([O:13]C(C)(C)C)=[N:11][CH:12]=1.[CH3:23][C:24]1[CH:40]=[CH:39][C:27]2[C:28](=O)[C:29]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:30]=3[CH2:31][CH2:32][C:26]=2[CH:25]=1>O1CCCC1>[CH3:37][C:34]1[CH:35]=[CH:36][C:29]2[CH:28]([C:7]3[C:8](=[O:18])[NH:9][C:10](=[O:13])[NH:11][CH:12]=3)[C:27]3[CH:39]=[CH:40][C:24]([CH3:23])=[CH:25][C:26]=3[CH:32]=[CH:31][C:30]=2[CH:33]=1

参加物

5

反応物 3

HCID 8188515-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidineHCID 2211720110,11-dihydro-2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-oneHCID 178418339Butyllithium

生成物 1

HCID 221172135-(2,8-Dimethyl-5h-dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
120 °C

実験手順

n-Butyllithium (5.6 ml of a 2.5M solution in hexanes) was added dropwise to a solution of 5-bromo-2,4-bis(1,1,-dimethylethoxy)pyrimidine (example 1 step (i)) (3.85 g) in tetrahydrofuran (30 ml) at -78° C. The solution was stirred for 30 minutes and a solution of 10,11-dihydro-2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-one (European Patent, 1993, 0 589 322 A1) (3.0 g) in tetrahydrofuran (20 ml) was added. The mixture was stirred at -78° C. for 45 minutes and room temperature for 15 minutes and then partitioned between brine and ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The residue was dissolved in glacial acetic acid (100 ml) and heated at 120° C. for 30 minutes. The solvent was evaporated and the residue azeotroped with toluene and triturated with diethyl ether to give a solid. Yield 4.03 g.

後処理

  1. stirringThe mixture was stirred at -78° C. for 45 minutes and room temperature for 15 minutes
  2. custompartitioned between brine and ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in glacial acetic acid (100 ml)
  6. customThe solvent was evaporated
  7. customthe residue azeotroped with toluene
  8. customtriturated with diethyl ether
  9. customto give a solid

出典と根拠

ORDレコード
ord-699c2f7b1b914936891c47c008b2fc04
出典データセット
uspto-grants-2000_12
特許番号
US06162808

関連ノート

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