Carbon Dioxide → 5-(Hydroxymethyl)-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 2181354ノート

反応式

HRID 2181354 の反応式
Br[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[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26].C([Mg]Br)C(C)C.[C:35](=O)=[O:36]>O1CCCC1>[OH:36][CH2:35][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[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26]

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 114429025-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneHCID 178418816HCID 178418816、化合物

生成物 1

HCID 102243115-(Hydroxymethyl)-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (3.6 g, Example 1c)) was dissolved in tetrahydrofuran (150 ml) at room temperature under an atmosphere of nitrogen. To this solution was added isobutyl magnesium bromide (4.9 mls, 2M in tetrahydrofuran). After 30 mins carbon dioxide gas was passed through the reaction and stirred for 2 hrs. The reaction mixture was then concentrated in vacuo and redissolved in ethanol (100 ml). Concentrated HCl (1 ml) was added and the reaction was heated at reflux for 36 hrs. The reaction was then concentrated in vacuo and partitioned between ethyl acetate and water. The organic layer was collected, dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The resultant gum was purified via chromotography eluting with 3:2 isohexane/diethyl ether to yield the sub title compound as a brown oil (2.3 g)

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionredissolved in ethanol (100 ml)
  3. additionConcentrated HCl (1 ml) was added
  4. temperaturethe reaction was heated
  5. temperatureat reflux for 36 hrs
  6. concentrationThe reaction was then concentrated in vacuo
  7. custompartitioned between ethyl acetate and water
  8. customThe organic layer was collected
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated to dryness in vacuo
  12. customThe resultant gum was purified via chromotography
  13. washeluting with 3:2 isohexane/diethyl ether

出典と根拠

ORDレコード
ord-60675db312b34a419b9896f69049d728
出典データセット
uspto-grants-2005_05
特許番号
US06890923B2

反応ノート

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