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

HRID 2257115

反応式

HRID 2257115 の反応式
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

参加物

6

反応物 2

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

生成物 1

HCID 293750Ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylate収率 46%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e0b8184e6eba483189c7564e33c8ae02
出典データセット
uspto-grants-1997_08
特許番号
US05656645

関連ノート

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