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

HRID 250101노트

반응식

HRID 250101 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-378ec0e344774003904321dea26beda5
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863291B2

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