N-bromobutanimide → [1,2]Thiazolo[4,3-d]pyrimidine

Reaction equation

C1C(=O)N(Br)C(=O)C1.N[C:10]1[N:15]=[CH:14][N:13](Cl)[C:12]2=[CH:17][NH:18][S:19][C:11]=12>>[N:18]1[S:19][CH:11]=[C:12]2[C:17]=1[CH:10]=[N:15][CH:14]=[N:13]2

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 22736822HCID 22736822, compound

Product 1

HCID 18630807[1,2]Thiazolo[4,3-d]pyrimidine

Procedure

Reaction of 4,6-dichloro-5-nitropyrimidine with CuCN/NMP gives the 4-nitrile. Reduction of the nitro group to the amine is followed by diazotization/thiation to give the corresponding 5-mercapto compound. Reaction of this with Me3Al/NH4Cl gives the amidine which is oxidatively cyclized with NBS to 7-amino-4-chloroisothiazolo[4,5-d]pyrimidine. Removal of the amino functionality by diazotization/hypophosphorus acid is followed by displacement of the 4-chlorine with an appropriate amine to give the desired isothiazolo[4,3-d]pyrimidine derivatives as shown above.

Workup

customRemoval of the amino functionality by diazotization/hypophosphorus acid

Sources & evidence

ORD record: ord-12184287a369445f86dd0d4261c6bc64
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521620B1

Reaction notes

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