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

HRID 1875966ノート

反応式

HRID 1875966 の反応式
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

参加物

5

反応物 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 57476592Ethyl (5-chlorothiazolo[5,4-d]pyrimidin-2-yl)carbamate

生成物 1

HCID 574765915-Methoxythiazolo[5,4-d]pyrimidin-2-amine収率 82%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-10111e8f23634a6daba4a7d1e7d0915a
出典データセット
uspto-grants-2012_11
特許番号
US08309577B2

反応ノート

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