Chloride → Thiazolo(4,5-d)pyrimidine

HRID 1059544Notes

Reaction equation

HRID 1059544 reaction equation
C[N+](C)=CCl.[Cl-].[Cl-].[CH2:8]([NH:10][C:11]([C:13]1[S:17][C:16](SC)=[N:15][C:14]=1[NH2:20])=O)C>>[S:17]1[C:13]2[CH:11]=[N:10][CH:8]=[N:20][C:14]=2[N:15]=[CH:16]1

Participants

4

Reactant 3

HCID 312ChlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 53935413Ethyl 2-methylthio-4-aminothiazole-5-carboxamide

Product 1

HCID 10351759Thiazolo(4,5-d)pyrimidine

Procedure

Reaction of N-cyanobismethylthiomethyleneimine with ethyl thioglycollate gives ethyl 2-methylthio-4-aminothiazole-5-carboxamide. Cyclization with formamide or equivalent, followed by desulfurization of the methylthio gives a thiazolopyrimidone, which can be activated by Vilsmeier reagent, and the chloride displaced by the desired amine to give the desired thiazolo[4,5-d]pyrimidine derivatives as shown above.

Sources & evidence

ORD record
ord-30dae55a690042f7a0e768b66a1bee87
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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