Urea → Thiazolo[4,5-d]pyrimidine-5,7-diol

HRID 1408460Notes

Reaction equation

HRID 1408460 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([O:9]C)=O.[NH2:11][C:12](N)=[O:13]>>[S:5]1[C:6]2[C:7](=[O:9])[NH:11][C:12](=[O:13])[NH:1][C:2]=2[N:3]=[CH:4]1

Participants

3

Reactant 2

HCID 1176UreaHCID 15832487Methyl 4-amino-1,3-thiazole-5-carboxylate

Product 1

HCID 345636Thiazolo[4,5-d]pyrimidine-5,7-diol

Conditions

Temperature
190 °C

Procedure

A mixture of methyl 4-aminothiazole-5-carboxylate (1.0 eq.) and urea (5 eq.) was heated at 190° C. for 2 hours. The hot reaction mixture was poured onto sodium hydroxide solution and any insoluble material was removed by filtration. The mixture was then acidified (HCl, 2N) to yield thiazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione as a white precipitate, which was collected by filtration and air dried.

Workup

  1. additionThe hot reaction mixture was poured onto sodium hydroxide solution
  2. customany insoluble material was removed by filtration

Sources & evidence

ORD record
ord-178b9de75f124024a65b1ded26c7f791
Source dataset
uspto-grants-2014_12
Patent number
US08921361B2

Reaction notes

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