Sodium ethoxide → HCID 46199897, compound

HRID 1930677Notes

Reaction equation

HRID 1930677 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[NH:15])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[C:17]1([CH:23]([CH3:30])[C:24](=O)[CH2:25][C:26](=O)[CH3:27])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O-]CC.[Na+]>C(O)C>[CH3:27][C:26]1[CH:25]=[C:24]([CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:30])[N:16]=[C:14]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([N:3]3[CH:4]=[CH:5][N:6]=[C:2]3[CH3:1])=[CH:12][CH:11]=2)[N:15]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 14007688HCID 14007688, compoundHCID 178432900HCID 178432900, compound

Product 1

HCID 46199897HCID 46199897, compoundYield 1.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)guanidine (953 mg, 4.43 mmol, example 9e), 5-phenylhexane-2,4-dione (842 mg, 4.43 mmol) and sodium ethoxide (301 mg, 4.43 mmol) in ethanol (5 mL) were heated in a microwave reactor at 100° C. for 15 minutes. The mixture was allowed to reach room temperature and the crude was purified by HPLC yielding 4-methyl-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-6-(1-phenylethyl)pyrimidin-2-amine (23.00 mg, 1.313%). MS (ES+) m/z 370.2 (M+H)+

Workup

  1. customto reach room temperature
  2. customthe crude was purified by HPLC

Sources & evidence

ORD record
ord-9e18f90929a34dc8ba06182db87ba131
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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