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

HRID 1365754Notes

Reaction equation

HRID 1365754 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 40 (WO 2006/096338; WO 2005/049613) and urea is heated at 190° C. for 2 hours. The hot reaction mixture is poured onto sodium hydroxide solution and any insoluble material is removed by filtration. The mixture is acidified (HCl, 2N) to yield thiazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione 41 (Baker et al (1970) Jour. of the Chem. Soc. 18:2478-84; U.S. Pat. No. 3,277,093; Childress and McKee (1951) J. Am. Chem. Soc. 73:3862-64; Erlenmeyer and Furger (1943) Helv. Chem. Acta 26:366-68) as a white precipitate, which was collected by filtration and air dried.

Workup

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

Sources & evidence

ORD record
ord-f78c393d3cb34bf89545fa9b150450c5
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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