5-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine → (+/-)-4-(2,4-Bis(1,1-dimethylethoxy)pyrimidin-5-yl)-7-ethyl-2-methyl-9,10-dihydro-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-ol

HRID 324414

反応式

HRID 324414 の反応式
Br[C:2]1[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:4][C:5]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[N:6][CH:7]=1.C([Li])CCC.[CH2:23]([C:25]1[CH:26]=[CH:27][C:28]2[C:38](=[O:39])[C:33]3[N:34]=[C:35]([CH3:37])[O:36][C:32]=3[CH2:31][CH2:30][C:29]=2[CH:40]=1)[CH3:24]>O1CCCC1>[CH3:10][C:9]([CH3:12])([O:8][C:5]1[N:4]=[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:2]([C:38]2([OH:39])[C:33]3[N:34]=[C:35]([CH3:37])[O:36][C:32]=3[CH2:31][CH2:30][C:29]3[CH:40]=[C:25]([CH2:23][CH3:24])[CH:26]=[CH:27][C:28]2=3)=[CH:7][N:6]=1)[CH3:11]

参加物

5

反応物 3

HCID 8188515-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidineHCID 220035847-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-oneHCID 178418339Butyllithium

生成物 1

HCID 70113732(+/-)-4-(2,4-Bis(1,1-dimethylethoxy)pyrimidin-5-yl)-7-ethyl-2-methyl-9,10-dihydro-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A stirred solution of the product from example 1 step (vi) (3.60 g) in tetrahydrofuran (30 ml) at −70° C. was treated dropwise with n-butyllithium (4.75 ml of a 2.5M solution in hexanes) and stirred for 30 minutes. A solution of the product from example 3 step (vi) (2.60 g) in tetrahydrofuran (30 ml) was added dropwise and the reaction stirred at room temperature for 3 hours. The reaction was partitioned between brine and ethyl acetate and the organics dried (MgSO4) and evaporation under reduced pressure gave a brown oil. Purification was by column chromatography eluting with 50% ethyl acetate in isohexane.

後処理

  1. stirringthe reaction stirred at room temperature for 3 hours
  2. customThe reaction was partitioned between brine and ethyl acetate
  3. customthe organics dried
  4. custom(MgSO4) and evaporation under reduced pressure
  5. customgave a brown oil
  6. customPurification
  7. washeluting with 50% ethyl acetate in isohexane

出典と根拠

ORDレコード
ord-de09f20e06da4423975a7f432516d2af
出典データセット
uspto-grants-2001_04
特許番号
US06218376B1

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