Ethyl Acetoacetate → 1-[2-[4-(6-methyl-4-oxo-1H-pyrimidin-2-yl)butoxy]pyrimidin-4-yl]-2-(2,2,2-trifluoroethyl)guanidine

HRID 2291323ノート

反応式

HRID 2291323 の反応式
Cl.[F:2][C:3]([F:24])([F:23])[CH2:4][N:5]=[C:6]([NH2:22])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH2:21])=[NH:20])[N:9]=1.[C:25](OCC)(=[O:30])[CH2:26][C:27]([CH3:29])=O.[H-].[Na+]>CO>[OH:30][C:25]1[CH:26]=[C:27]([CH3:29])[N:21]=[C:19]([CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:10]2[N:9]=[C:8]([NH:7][C:6]([NH2:22])=[N:5][CH2:4][C:3]([F:2])([F:23])[F:24])[CH:13]=[CH:12][N:11]=2)[N:20]=1

参加物

5

反応物 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 212797305-(4-[2-(2,2,2-Trifluoroethyl)guanidino]pyrimid-2-yloxy)valeramidine hydrochloride

生成物 1

HCID 1784293291-[2-[4-(6-methyl-4-oxo-1H-pyrimidin-2-yl)butoxy]pyrimidin-4-yl]-2-(2,2,2-trifluoroethyl)guanidine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

5-(4-[2-(2,2,2-Trifluoroethyl)guanidino]pyrimid-2-yloxy)valeramidine hydrochloride (0.5 g.) was added to a solution of ethyl acetoacetate (0.352 g.) and sodium hydride (0.07 g.) in MeOH (6 ml.). The resulting solution was heated under reflux for 18 hours. The solvent was evaporated and the residue taken up in aqueous HOAc and extracted with EtOAc. The aqueous layer was basified with potassium carbonate and extracted with EtOAc. Work up gave a sticky solid which was crystallised from acetonitrile to give 4-hydroxy-6-methyl-2-[4-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yloxy)butyl]pyrimidine as white crystals (0.22 g.), m.p. 191°-193°.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvent was evaporated
  4. extractionextracted with EtOAc
  5. extractionextracted with EtOAc
  6. customWork up gave a sticky solid which
  7. customwas crystallised from acetonitrile

出典と根拠

ORDレコード
ord-d59c1714b7d948489e92c494d080fd47
出典データセット
uspto-grants-1989_01
特許番号
US04795755

反応ノート

読み込み中…