Sodium Hydroxide → (3-Imidazol-1-yl-phenyl)-(4-pyridin-3-yl-pyrimidin-2-yl)-amine

HRID 973802Notes

Reaction equation

HRID 973802 reaction equation
Cl.Cl.[N:3]1([C:8]2[CH:9]=[C:10]([NH:14][C:15]([NH2:17])=[NH:16])[CH:11]=[CH:12][CH:13]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.CN(C)[CH:20]=[CH:21][C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=O.[OH-].[Na+]>C(O)CC>[N:3]1([C:8]2[CH:9]=[C:10]([NH:14][C:15]3[N:17]=[C:22]([C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:21]=[CH:20][N:16]=3)[CH:11]=[CH:12][CH:13]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178478791[3-(1H-Imidazol-1-yl)phenyl]guanidine, dihydrochloride

Product 1

HCID 11723151(3-Imidazol-1-yl-phenyl)-(4-pyridin-3-yl-pyrimidin-2-yl)-amineYield 67%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Two and 73 hundredths grams of [3-(1H-imidazol-1-yl)phenyl]guanidine, dihydrochloride (2) from Example 1, 1.76 grams of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one, 25 ml of n-propanol and 2 equivalents (2 ml) of 10N NaOH at pH=11 is refluxed for twenty-four (24) hours. The products are isolated by quenching the reaction mixture including any precipitated solids into water followed by filtration. These filtered solids are re-suspended in water to remove inorganic salts, filtered and air dried to give 2.1 g (67% yield) of the desired product, mp 95°-120° C.

Workup

  1. customThe products are isolated
  2. customby quenching the reaction mixture
  3. filtrationfollowed by filtration
  4. customto remove inorganic salts
  5. filtrationfiltered
  6. customair dried

Sources & evidence

ORD record
ord-828f52cf32c94d2c877cadb2251399e6
Source dataset
uspto-grants-1991_11
Patent number
US05064963

Reaction notes

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