Water → 5-Aminothiazolo[4,5-d]pyrimidine-2(3H)-thione

HRID 505841Notes

Reaction equation

HRID 505841 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5](Br)=[CH:4][N:3]=1.CCO[C:13]([S-:15])=[S:14].[K+].O.OS(O)(=O)=O>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:15][C:13](=[S:14])[NH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 2735045Potassium ethylxanthateHCID 234235905-Bromopyrimidine-2,4-diamine

Product 1

HCID 577560685-Aminothiazolo[4,5-d]pyrimidine-2(3H)-thioneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2,4-diamino-5-bromo-pyrimidine (0.95 g, 5 mmol, 1.0 eq) and potassium ethyl xanthogenate (1.6 g, 10 mmol. 2.0 eq) in DMF (30 ml) heated up to reflux for 10 hours under N2. The reaction solution was cooled down to room temperature (about 25° C.) and water (30 ml) was added to the solution. The pH of the solution was adjusted to about 5 with 3.6 N H2SO4. The resulting mixture was heated up to 50-60° C. for 1 hour, cooled to room temperature stirred for 2 hours, filtered, washed with water (20 ml) and ethanol (20 ml) and dried to give 0.8 g (87%) of 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-thione as a yellow solid. 1H NMR, HPLC and LCMS analyses of this product are identical to the product described in Step 2 of Example 1.

Workup

  1. temperatureto reflux for 10 hours under N2
  2. additionwas added to the solution
  3. temperaturecooled to room temperature
  4. filtrationfiltered
  5. washwashed with water (20 ml) and ethanol (20 ml)
  6. customdried

Sources & evidence

ORD record
ord-f250254421c745dc8f7047b5fe0223a4
Source dataset
uspto-grants-2010_08
Patent number
US07781581B2

Reaction notes

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