Guanidine Hydrochloride → 4-(2-Furyl)-5-(4-pyridyl)-2-pyrimidinyl amine

HRID 457875Notes

Reaction equation

HRID 457875 reaction equation
CN(C)[CH:3]=[C:4]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.Cl.[NH2:20][C:21]([NH2:23])=[NH:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]1[C:4]([C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[CH:3][N:20]=[C:21]([NH2:23])[N:22]=1

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 670738543-(Dimethylamino)-1-(furan-2-yl)-2-(pyridin-4-yl)prop-2-en-1-one

Product 1

HCID 97947204-(2-Furyl)-5-(4-pyridyl)-2-pyrimidinyl amineYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 3-(dimethylamino)-1-(2-furyl)-2-(4-pyridyl)-2-propene-1-one (2.2 g, 9.08 mmol), guanidine hydrochloride (2.6 g, 27.2 mmol) and potassium carbonate (7.5 g, 54.3 mmol) in N,N-dimethylformamide (20 mL) was stirred at 70° C. for 12 hours. After cooling as it was, the reaction mixture was diluted with water. The resulting crystals were collected by filtration and washed with water, to give the title compound (1.73 g, 80%) as a pale yellow solid.

Workup

  1. temperatureAfter cooling as it
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-6d8106a2920646acb514d843bfc9b85c
Source dataset
uspto-grants-2007_03
Patent number
US07189717B2

Reaction notes

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