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

HRID 505837Notes

Reaction equation

HRID 505837 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 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4-diamino-5-bromo-pyrimidine (9.5 g, 50 mmol, 1.0 eq) and potassium ethyl xanthogenate (16 g, 100 mmol. 2 eq) in DMF (300 ml) was heated up to reflux for 10 hours under N2. The reaction solution was cooled down to room temperature and water (600 ml) was added. The pH of the solution was then adjusted to about 5 using H2SO4 (2 ml) and the resulting suspension was stirred at 50-60° C. for 30 min., cooled to about 30° C., filtered and washed with water. The product was dried under vacuum at 50-60° C. to give 8.2 g (89%) of 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-thione as a yellow solid. 1H NMR (400 MHz, d6-DMSO). δ 6.91 (s, 2H, ex. D2O), 8.34 (s, 1H), 12.3 (br, 1H, ex. D2O); MS (+)-ES [M+H]+ m/z 185.

Workup

  1. temperatureto reflux for 10 hours under N2
  2. temperaturecooled to about 30° C.
  3. filtrationfiltered
  4. washwashed with water
  5. customThe product was dried under vacuum at 50-60° C.

Sources & evidence

ORD record
ord-c5173950fb0c424f938c28774f8155b8
Source dataset
uspto-grants-2010_08
Patent number
US07781581B2

Reaction notes

Loading…