Water → 5-methoxy-Thiazolo[5,4-d]pyrimidin-2-amine

HRID 250101Notes

Reaction equation

HRID 250101 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[C:9]([NH:11]C(=O)OCC)[S:8][C:6]=2[N:7]=1.[CH3:17][O-:18].[Na+].O>CO>[CH3:17][O:18][C:2]1[N:3]=[CH:4][C:5]2[N:10]=[C:9]([NH2:11])[S:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 57476592HCID 57476592, compound

Product 1

HCID 574765915-methoxy-Thiazolo[5,4-d]pyrimidin-2-amineYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethyl 5-chlorothiazolo[5,4-d]pyrimidin-2-ylcarbamate (250 mg, 0.966 mmol) was suspended in MeOH (10 mL) and a 25% (w/w) solution of sodium methoxide in methanol was added (10 mL, 46.3 mmol). The resulting solution was refluxed overnight, cooled to ambient temperature, poured into an equal volume of water and extracted with chloroform (4×). A significant amount of compound was still present in the aqueous phase, so this was concentrated to residue, and then dissolved in a small amount of 1N HCl (not enough to make the resulting solution acidic) and extracted again with EtOAc (5×). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. 5-Methoxythiazolo[5,4-d]pyrimidin-2-amine (144 mg, 0.790 mmol, 82% yield) was thus obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (s, 1H) 7.81 (s, 2H) 3.90 (s, 3H). MS (LC/MS) R.T.=0.73; [M+H]+=183.03.

Workup

  1. temperatureThe resulting solution was refluxed overnight
  2. extractionextracted with chloroform (4×)
  3. concentrationso this was concentrated to residue
  4. dissolutiondissolved in a small amount of 1N HCl (not enough
  5. extractionextracted again with EtOAc (5×)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-378ec0e344774003904321dea26beda5
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

Loading…