Acetone → HCID 20435498, compound

HRID 1153939Notes

Reaction equation

HRID 1153939 reaction equation
[C:1]([CH:6]([CH2:10]C#C)[C:7](=O)[CH3:8])([O:3][CH2:4][CH3:5])=O.C(=O)(O)O.[NH2:17][C:18](N)=[NH:19].C(O)C.CC(C)=O>CS(C)=O>[CH3:8][C:7]1[C:6]2[CH:10]=[C:4]([CH3:5])[O:3][C:1]=2[N:17]=[CH:18][N:19]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 702EthanolHCID 286947Carbonic acid-guanidine (1:1)HCID 10964906HCID 10964906, compound

Product 1

HCID 20435498HCID 20435498, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 6.0 g 3-carbethoxy-5-hexyn-2-one and 3.6 g guanidine carbonate was heated in 9 ml dimethylsulfoxide under a nitrogen atmosphere at 140° for 4 hours. The ethanol produced in the reaction was removed as it was formed by distillation. After cooling to room temperature, acetone was added then the crystalline solid was collected then rinsed with water to yield 2.6 g of 4,6-dimethylfuro[2,3-d]pyrimidine; m.p. 262°-263°. Absorptions at 2.55 (singlet), 2.82 (singlet) and 6.58 (broadened singlet) ppm in the nuclear magnetic resonance spectrum (60 MHz) indicated the title compound.

Workup

  1. customwas removed as it
  2. customwas formed by distillation
  3. customthe crystalline solid was collected
  4. washthen rinsed with water

Sources & evidence

ORD record
ord-42f19fc85ff748fb8ba3240fae187f04
Source dataset
uspto-grants-1984_12
Patent number
US04487626

Reaction notes

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