2-Methyl-2-butene → 2-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carboxylic acid

HRID 2171793ノート

反応式

HRID 2171793 の反応式
[CH3:1][C:2]1([CH3:20])[CH2:7][CH2:6][CH:5]([C:8]2[S:9][C:10]3[N:11]=[C:12]([CH3:19])[N:13]=[C:14]([CH:17]=[O:18])[C:15]=3[N:16]=2)[CH2:4][CH2:3]1.CC(=CC)C.[O-:26]Cl=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CC(C)=O.O>[CH3:1][C:2]1([CH3:20])[CH2:3][CH2:4][CH:5]([C:8]2[S:9][C:10]3[N:11]=[C:12]([CH3:19])[N:13]=[C:14]([C:17]([OH:26])=[O:18])[C:15]=3[N:16]=2)[CH2:6][CH2:7]1

参加物

8

反応物 5

HCID 105532-Methyl-2-buteneHCID 24436Sodium SulfateHCID 24477Sodium ThiosulfateHCID 23668197Sodium ChloriteHCID 1180239142-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carbaldehyde

生成物 1

HCID 1180240312-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carboxylic acid

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

To a mixture of [2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methanol (500 mg) and DCM (10 mL) was added Dess-Martin periodinane (1.46 g) under ice-cooling, followed by stirring at 0° C. for 3 hours. To the reaction mixture was added an aqueous Na2S2O3 solution, followed by extraction with DCM. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over Na2SO4, and then concentrated under reduced pressure to obtain 2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carbaldehyde (492 mg). To a mixture of the obtained aldehyde, NaH2PO4 (245 mg), 2-methyl-2-butene (542 μL), water (5 mL), and acetone (10 mL) was added NaClO2 (231 mg) under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction mixture were added an aqueous Na2S2O3 solution and Na2SO4, followed by extraction with a mixed solution (1:9) of 2-propanol and chloroform. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure to obtain 2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carboxylic acid (870 mg).

後処理

  1. temperaturecooling
  2. extractionfollowed by extraction with a mixed solution (1:9) of 2-propanol and chloroform
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4b2dc470b0ca4398b0acfe49c2b36a50
出典データセット
uspto-grants-2015_06
特許番号
US09051339B2

反応ノート

読み込み中…