Diethyl (ethoxymethylene)malonate → Ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylate

HRID 2257115

반응식

HRID 2257115 반응식
C(O)(=O)C.[C:5]([NH2:8])(=[NH:7])[CH3:6].C([O:11][CH:12]=[C:13]([C:19](OCC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>C(O)C.O.ClCCl>[CH3:6][C:5]1[NH:7][C:12](=[O:11])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:19][N:8]=1

참가 물질

6

반응물 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 160356Ethanimidamide, acetate (1:1)2회

생성물 1

HCID 293750Ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylate수율 46%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Acetamidine acetate (37.21 g, 0.31 mole) and diethyl ethoxymethylenemalonate (63 mL, 0.31 mole) were refluxed for 4 h in ethanol (60 mL). The reaction mixture was allowed to cool for 15 min., then acetamidine acetate (37.21 g, 0.31 mole) was added. The reaction mixture was refluxed for 22 hours, allowed to cool to room temperature, and diluted with water (200 mL) and dichloromethane (200 mL). The aqueous layer was extracted with 10% isopropanol/dichloromethane (2×200 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried over magnesium sulfate, filtered and the solvent was removed. The residue was recrystallized from chloroform/hexanes in two crops to afford the title compound (24.92 g) in 46% yield as yellowish crystals. Rf =0.27 (silica gel, 10% isopropanol in dichloromethane). m.p. 187°-188° C.

후처리

  1. temperatureto cool for 15 min.
  2. temperatureThe reaction mixture was refluxed for 22 hours
  3. extractionThe aqueous layer was extracted with 10% isopropanol/dichloromethane (2×200 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed
  8. customThe residue was recrystallized from chloroform/hexanes in two crops

출처 및 근거

ORD 기록
ord-e0b8184e6eba483189c7564e33c8ae02
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05656645

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