Potassium Carbonate → 4-(methoxy(phenyl)methyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine

HRID 1930697노트

반응식

HRID 1930697 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[NH:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.C(=O)([O-])[O-].[K+].[K+].[CH3:25][O:26][CH:27]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:28]([CH:30]1[C:35](=O)[CH2:34][CH2:33][O:32][CH2:31]1)=O>C(O)C>[CH3:25][O:26][CH:27]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:28]1[C:30]2[CH2:31][O:32][CH2:33][CH2:34][C:35]=2[N:17]=[C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:18]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 593336923-(2-Methoxy-2-phenylacetyl)dihydro-2H-pyran-4(3H)-oneHCID 178493227HCID 178493227, 화합물

생성물 1

HCID 593337054-(methoxy(phenyl)methyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine수율 2.7%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
50 °C

실험 절차

A reaction mixture of 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (0.300 g, 0.81 mmol) and potassium carbonate (0.337 g, 2.44 mmol) in ethanol (5 mL) was stirred at 50° C. for 5 minutes. 3-(2-methoxy-2-phenylacetyl)dihydro-2H-pyran-4(3H)-one (0.161 g, 0.65 mmol) in ethanol (0.5 mL) was added dropwise to the reaction mixture and the resulting mixture was stirred at 50° C. overnight. The solvent was evaporated and the residue was partitioned between water and dichloromethane. The water phase was extracted twice with dichloromethane. The combined organic layer was dried over MgSO4, filtered, concentrated and purified by preparative HPLC yielding 4-(methoxy(phenyl)methyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine (8.00 mg, 2%).

후처리

  1. stirringthe resulting mixture was stirred at 50° C. overnight
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water and dichloromethane
  4. extractionThe water phase was extracted twice with dichloromethane
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-723434d57d5d4f2087b5a7e31d4ac91b
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188101B2

반응 노트

불러오는 중…