Dimethyl Sulfoxide → Pyrimidine

HRID 2118622Notes

Reaction equation

HRID 2118622 reaction equation
[C:1](=[O:4])(O)O.[NH2:5][C:6]([NH2:8])=N.CS(C)=O.C[N:14]([CH3:17])[CH:15]=O.C[N:19]([CH3:23])[C:20](=O)[CH3:21]>>[N:8]1[C:6]2[CH:20]=[CH:21][O:4][C:1]=2[CH:17]=[N:14][CH:15]=1.[N:19]1[CH:20]=[CH:21][CH:6]=[N:5][CH:23]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6228DimethylformamideHCID 31374DimethylacetamideHCID 286947Carbonic acid-guanidine (1:1)

Product 2

HCID 9260PyrimidineHCID 21948582Furo[3,2-d]pyrimidine

Procedure

Reacting XIX with an excess of guanidine carbonate in an organic solvent, preferably a polar aprotic solvent such as dimethylsulfoxide (DMSO), dimethylformamide (DMF), or N,N-dimethylacetamide, at a temperature of 80° to 200°, preferably 100° to 160°, ambient pressure and preferably under an inert atmosphere, yields both XXI and XX as products. The products are isolated upon dilution of the reaction mixture with, for example, acetone and water successively. Higher reaction temperatures and longer reaction times (e.g., in DMSO at 130°-150° for 2 to 8 hours) favor the production of the furopyrimidine XXI over the uncyclized pyrimidine XX.

Sources & evidence

ORD record
ord-a6d22e76ea554a5ba3234a6de7101a56
Source dataset
uspto-grants-1987_07
Patent number
US04680053

Reaction notes

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