Sodium Hydroxide → 4-(2-furanyl)-N-[3-(1H-imidazol-1-yl)phenyl]-2-pyrimidinamine

HRID 973804Notes

Reaction equation

HRID 973804 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]=[C:21](C)[C:22]([C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)=O.[OH-].[Na+]>C(O)CC>[O:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[C:22]1[CH:21]=[CH:20][N:17]=[C:15]([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([N:3]3[CH:7]=[CH:6][N:5]=[CH:4]3)[CH:9]=2)[N:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 545305473-Dimethylamino-1-(2-furyl)-2-methyl-2-propen-1-oneHCID 178478791[3-(1H-Imidazol-1-yl)phenyl]guanidine, dihydrochloride

Product 1

HCID 143471164-(2-furanyl)-N-[3-(1H-imidazol-1-yl)phenyl]-2-pyrimidinamineYield 44.5%

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, 1.6 grams of 3-dimethylamino-1-(2-furyl)-2-methyl-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 1.35 g (44.5% yield) of the desired product, mp 175°-178° 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-7266d8bf9d2840cc9f0c2399a93dfef6
Source dataset
uspto-grants-1991_11
Patent number
US05064963

Reaction notes

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