Dichloromethane → 5-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 2181347

反応式

HRID 2181347 の反応式
[Br:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]=2[S:4][C:3]=1[CH:18](O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26].FC(F)(F)C(O)=O.C(Cl)Cl>C([SiH](CC)CC)C>[Br:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:5]=2[S:4][C:3]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:26])([F:27])[F:28]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 52825285-Bromo-6-[hydroxy[2-(trifluoromethyl)phenyl]methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

生成物 1

HCID 114429025-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione収率 84.5%

試薬・触媒・溶媒 1

HCID 12052Triethylsilane溶媒

実験手順

5-Bromo-6-{hydroxy[2-(trifluoromethyl)phenyl]methyl}-1-isobutyl-3-methyl-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (33.47 g) was dissolved in triethyl silane (100 mls) and cooled to 0° C. before trifluoroacetic acid (100 mls) was added dropwise. After complete addition the resultant thick suspension was diluted by the addition of DCM (100 mls) and the reaction was stirred at room temperature for 18 hours. The reaction mixture was then concentrated in vacuo and partitioned between DCM and 50% aqueous sodium hydrogen carbonate. The organic layer was collected, dried over magnesium sulfate, filtered and concentrated in vacuo. The resultant off white solid was stirred vigorously with isohexane for 1 hour before being collected by filtration to yield 27.286 g (84.5%) of the subtitle compound.

後処理

  1. additionwas added dropwise
  2. additionAfter complete addition the resultant thick suspension
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. custompartitioned between DCM and 50% aqueous sodium hydrogen carbonate
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. stirringThe resultant off white solid was stirred vigorously with isohexane for 1 hour
  10. filtrationbefore being collected by filtration

出典と根拠

ORDレコード
ord-0ab8523d44fa4123b1094f5e6afdf4e9
出典データセット
uspto-grants-2005_05
特許番号
US06890923B2

関連ノート

読み込み中…