Diisopropyl Ether → N-{4-[6-amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)pyrimidin-4-yl]phenyl}acetamide

HRID 1172261

反応式

HRID 1172261 の反応式
[NH2:1][C:2]([NH2:4])=[S:3].[C:5]([C:7]([C:19]#[N:20])=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=1)#[N:6].[C:21](=O)(O)[O-].[Na+].[CH2:26]1[C:31](=O)[N:30](Br)[C:28](=O)[CH2:27]1.[CH:34](OC(C)C)(C)[CH3:35]>C(O)C>[NH2:6][C:5]1[N:4]=[C:2]([S:3][CH2:21][C:31]2[CH:26]=[CH:35][CH:34]=[C:28]([CH3:27])[N:30]=2)[N:1]=[C:8]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)[C:7]=1[C:19]#[N:20]

参加物

7

反応物 5

HCID 7914Diisopropyl EtherHCID 33296N-(4-(2,2-Dicyanoethenyl)phenyl)acetamideHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 2723790Thiourea

生成物 1

HCID 11581892N-{4-[6-amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)pyrimidin-4-yl]phenyl}acetamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

The portion (4.56 g) was dissolved in 50 mL of ethanol, 1.72 g of thiourea was added to the solution, and the mixture was heated to reflux for 1 hour. Next, to the reaction solution added 20 mL of ethanol and the solution was cooled, and further 4.79 g of N-[4-(2,2-dicyanovinyl)phenyl]acetamide and 3 g of sodium bicarbonate were added thereto, and then the mixture was heated to reflux for 1.5 hours. After the reaction solution was allowed to cool, 2.02 g of NBS was added to the solution, and the mixture was heated to reflux for 30 minutes. After reaction solution was allowed to cool, furthermore diisopropyl ether was added thereto, and the inorganic material precipitated was filtrated off, then the filtrate was again concentrated and dissolved in ethanol. Saturated aqueous sodium bicarbonate was added to the solution and the resulting crystal was filtrated, washed with water and ethanol, and then dried under reduced pressure to give 3.2 g of N-{4-[6-amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)pyrimidin-4-yl]phenyl}acetamide as a white powder.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturethe solution was cooled
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 1.5 hours
  6. temperatureto cool
  7. temperaturethe mixture was heated
  8. temperatureto reflux for 30 minutes
  9. customAfter reaction solution
  10. temperatureto cool
  11. customthe inorganic material precipitated
  12. filtrationwas filtrated off
  13. concentrationthe filtrate was again concentrated
  14. dissolutiondissolved in ethanol
  15. additionSaturated aqueous sodium bicarbonate was added to the solution
  16. filtrationthe resulting crystal was filtrated
  17. washwashed with water and ethanol
  18. customdried under reduced pressure

出典と根拠

ORDレコード
ord-c81a4d0915304f49b543c6775c31d5d7
出典データセット
uspto-grants-2010_11
特許番号
US07834002B2

関連ノート

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