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 1930697Notes

Reaction equation

HRID 1930697 reaction equation
[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

Participants

5

Reactant 3

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

Product 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-amineYield 2.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-723434d57d5d4f2087b5a7e31d4ac91b
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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