Guanidine Hydrochloride → 4-(2-Furyl)pyrimidin-2-amine

HRID 747149Notes

Reaction equation

HRID 747149 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.Cl.[NH2:14][C:15]([NH2:17])=[NH:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]1[CH:4]=[CH:3][N:14]=[C:15]([NH2:17])[N:16]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 535936HCID 535936, compound

Product 1

HCID 38049894-(2-Furyl)pyrimidin-2-amineYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3-(dimethylamino)-1-(2-furyl)-2-propen-1-one (5.0 g, 30.3 mmol), guanidine hydrochloride (5.8 g, 60.7 mmol) and potassium carbonate (8.4 g, 60.9 mmol) in N,N-dimethylformamide (50 ml) was stirred at 100° C. for 21 hours. After cooling as it was, the reaction mixture was diluted with ice water (250 ml). The resulting solid was collected by filtration and washed with water, to give the title compound (4.19 g, 86%) as a pale brown solid.

Workup

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

Sources & evidence

ORD record
ord-ba7a7b4ac8394a0d8d1decdb2490eafb
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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