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

HRID 1930700Notes

Reaction equation

HRID 1930700 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+].[O:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[CH2:30][CH2:31][C:32]([CH:34]1[C:39](=O)[CH2:38][CH2:37][O:36][CH2:35]1)=O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:18]=[C:32]([CH2:31][CH2:30][CH:26]3[CH2:27][CH2:28][CH2:29][O:25]3)[C:34]3[CH2:35][O:36][CH2:37][CH2:38][C:39]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 593337093-(3-(tetrahydrofuran-2-yl)propanoyl)dihydro-2H-pyran-4(3H)-oneHCID 178493227HCID 178493227, compound

Product 1

HCID 59333806N-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amineYield 1.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A reaction mixture of 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (0.305 g, 0.83 mmol, example 7c) and potassium carbonate (0.343 g, 2.48 mmol) in ethanol (3 mL) was stirred at 50° C. for 20 minutes under argon. 3-(3-(tetrahydrofuran-2-yl)propanoyl)dihydro-2H-pyran-4(3H)-one (0.187 g, 0.83 mmol) was added dropwise (neat) over 2 hours and stirred at 50° C. overnight. The solvent was evporated 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 and concentrated. ¼ of the crude was purified by preparative HPLC and concentrated. The residue was partitioned between NaHCO3 (aq) and dichloromethane and the the water phase was extracted twice with dichloromethane, dried (MgSO4) and concentrated giving 4 mg of the product.

Workup

  1. stirringstirred at 50° C. overnight
  2. customthe residue was partitioned between water and dichloromethane
  3. extractionThe water phase was extracted twice with dichloromethane
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customwas purified by preparative HPLC
  8. concentrationconcentrated
  9. customThe residue was partitioned between NaHCO3 (aq) and dichloromethane
  10. extractionthe the water phase was extracted twice with dichloromethane
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-27d7c325335b4ac9822641de35232ed9
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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