Methanol → 7-Methoxy-5-methylthiazolo[5,4-d]pyrimidin-2-amine

HRID 250112Notes

Reaction equation

HRID 250112 reaction equation
Cl[C:2]1[C:3]2[N:11]=[C:10]([NH:12]C(=O)OCC)[S:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[CH3:18][O-:19].[Na+].CO>O>[CH3:18][O:19][C:2]1[C:3]2[N:11]=[C:10]([NH2:12])[S:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 57476594Ethyl (7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-yl)carbamate

Product 1

HCID 574765957-Methoxy-5-methylthiazolo[5,4-d]pyrimidin-2-amineYield 55.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-ylcarbamate (300 mg, 1.100 mmol) was suspended in a 25% w/w solution of sodium methoxide in methanol (5 mL, 23.14 mmol) and the mixture was refluxed overnight. The mixture was cooled to ambient temperature, diluted with water and extracted with chloroform (4×). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford 7-methoxy-5-methylthiazolo[5,4-d]pyrimidin-2-amine (120 mg, 0.612 mmol, 55.6% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.71 (s, 2 H) 3.98 (s, 3 H) 2.52 (s, 3 H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. extractionextracted with chloroform (4×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-858fc6b9c5354aa691ade02b8c932938
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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