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

HRID 1930706Notes

Reaction equation

HRID 1930706 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][C:26]1[CH:30]=[C:29]([CH3:31])[N:28]([CH:32]([CH3:42])[C:33]([CH:35]2[C:40](=O)[CH2:39][CH2:38][O:37][CH2:36]2)=O)[N:27]=1>CCO>[CH3:25][C:26]1[CH:30]=[C:29]([CH3:31])[N:28]([CH:32]([C:33]2[C:35]3[CH2:36][O:37][CH2:38][CH2:39][C:40]=3[N:17]=[C:16]([NH:15][C:5]3[CH:6]=[CH:7][C:8]([N:9]4[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[N:18]=2)[CH3:42])[N:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 593337123-(2-(3,5-dimethyl-1H-pyrazol-1-yl)propanoyl)dihydro-2H-pyran-4(3H)-oneHCID 178493227HCID 178493227, compound

Product 1

HCID 593337114-(1-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amineYield 3.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (86 mg, 0.28 mmol) and potassium carbonate (77 mg, 0.56 mmol) in EtOH (7 mL) were heated to 60° C. for 10 min followed by the addition of 3-(2-(3,5-dimethyl-1H-pyrazol-1-yl)propanoyl)dihydro-2H-pyran-4(3H)-one (70 mg, 0.28 mmol). The reaction was stirred over night. Solvent was evaporated and the crude product was taken up in DCM and washed with water. The product was purified on a prepHPLC yielding 4-(1-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine (5.00 mg, 3.89%). MS (ES+) m/z 460.2 (M+H)+

Workup

  1. customSolvent was evaporated
  2. washwashed with water
  3. customThe product was purified on

Sources & evidence

ORD record
ord-85365fdbd7fe497cb21e74997865b571
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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