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

HRID 2291323노트

반응식

HRID 2291323 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-d59c1714b7d948489e92c494d080fd47
출처 데이터셋
uspto-grants-1989_01
특허 번호
US04795755

반응 노트

불러오는 중…