Acetone → 4,6-Dimethylfuro[2,3-d]pyrimidin-2-amine

HRID 1153938Notes

Reaction equation

HRID 1153938 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]([NH2:20])=[NH:19].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]=[C:18]([NH2:20])[N:19]=1

Participants

5

Reactant 3

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

Product 1

HCID 5958504,6-Dimethylfuro[2,3-d]pyrimidin-2-amineYield 8.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4.0 g 3-carbethoxy-5-hexyn-2-one and 2.4 g guanidine carbonate was heated in 6 ml dimethylsulfoxide under a nitrogen atmosphere at 110°-120° for 2 hours. The solution was then cooled, acetone added and the solid collected then rinsed with water to afford 0.27 g of 4,6-dimethylfuro[2,3-d]pyrimidin-2-amine: m.p. 263°-265°. The above filtrates were diluted further with water and the deposited solid was collected and dried to give 0.44 g of 2-amino-6-methyl-5-(2-propynyl)-4(3H)pyrimidinone, m.p. 245°-249°. Absorptions at 2.1 (triplet), 2.55 (singlet), and 3.45 (doublet) ppm in the nuclear magnetic resonance spectrum (60 MHz) indicated the title compound.

Workup

  1. temperatureThe solution was then cooled
  2. customthe solid collected
  3. washthen rinsed with water

Sources & evidence

ORD record
ord-9e2957f346dd42f088d0e19b35c3732c
Source dataset
uspto-grants-1984_12
Patent number
US04487626

Reaction notes

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