Methyl 3-amino-4-methylthiophene-2-carboxylate → 7-Methylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

HRID 736326

반응식

HRID 736326 반응식
CO[C:3]([C:5]1[S:6][CH:7]=[C:8]([CH3:11])[C:9]=1[NH2:10])=[O:4].[O-:12][C:13]#[N:14].[K+]>C(O)(=O)C.O>[CH3:11][C:8]1[C:9]2[NH:10][C:13](=[O:12])[NH:14][C:3](=[O:4])[C:5]=2[S:6][CH:7]=1

참가 물질

5

반응물 2

HCID 123584Methyl 3-amino-4-methylthiophene-2-carboxylateHCID 11378442Potassium cyanate

생성물 1

HCID 103523177-Methylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione수율 71.4%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

To a stirred solution of methyl-3-amino-4-methylthiophene-2-carboxylate (530 mg, 3.1 mmol) in acetic acid (15.5 mL) and water (1.6 mL) was added a solution of potassium cyanate (754 mg, 9.3 mmol) dissolved in water (2.5 mL) dropwise via syringe. The reaction was stirred at room temperature for 15 h, upon completion of the reaction; the reaction mixture was concentrated to 75% and filtered off white solid. To the solid was added 6% aqueous sodium hydroxide (16 mL) and refluxed for 2 h. After cooling to room temperature, the solution was acidified using 12N HCl to pH=6. The resultant precipitate was filtered, washed with water and dried in vacuum oven overnight to give 403 mg (71%) of the title compound as a white solid which was used without any further purification:

후처리

  1. concentrationthe reaction mixture was concentrated to 75%
  2. filtrationfiltered off white solid
  3. additionTo the solid was added 6% aqueous sodium hydroxide (16 mL)
  4. temperaturerefluxed for 2 h
  5. temperatureAfter cooling to room temperature
  6. filtrationThe resultant precipitate was filtered
  7. washwashed with water
  8. customdried in vacuum oven overnight

출처 및 근거

ORD 기록
ord-d931c3c2f13d48709d6d6f3053c4c064
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595324B2

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