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 2181354노트

반응식

HRID 2181354 반응식
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]

참가 물질

5

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-60675db312b34a419b9896f69049d728
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06890923B2

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