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 1930697ノート

反応式

HRID 1930697 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 593336923-(2-Methoxy-2-phenylacetyl)dihydro-2H-pyran-4(3H)-oneHCID 178493227HCID 178493227、化合物

生成物 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-amine収率 2.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-723434d57d5d4f2087b5a7e31d4ac91b
出典データセット
uspto-grants-2012_05
特許番号
US08188101B2

反応ノート

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