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

HRID 227440Notes

Reaction equation

HRID 227440 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[K+].C(O[C:14]([S-:16])=[S:15])C.O.Cl>CN(C=O)C>[NH2:8][C:5]1[N:6]=[CH:7][C:2]2[S:16][C:14](=[S:15])[NH:9][C:3]=2[N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2735045Potassium ethylxanthateHCID 234235905-Bromopyrimidine-2,4-diamine

Product 1

HCID 577560685-Aminothiazolo[4,5-d]pyrimidine-2(3H)-thioneYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-pyrimidine-2,4-diamine (2.0 g, 10.58 mmol) [prepared in a manner similar to English et. al. J. Am. Chem. Soc. 1946, 68, 453-458] and O-ethylxanthic acid potassium salt (3.39 g, 21.16 mmol) was heated in DMF (25 mL) to 140° C. After 5 h the reaction was cooled to ambient temperature and 25 mL of water was added. The pH was then adjusted to 5.0 using I N HCl. A red precipitate formed and was collected by filtration, yielding 900 mg (30%) of a solid: 1H NMR (400 MHz, d6-DMSO) δ 13.85 (s, 1H), 8.33 (br s, 1H), 6.90 (s 2H).

Workup

  1. customA red precipitate formed
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-e6c9f81d65dc42f88f86a46cf9686d97
Source dataset
uspto-grants-2009_07
Patent number
US07560544B2

Reaction notes

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