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

HRID 1251356

反応式

HRID 1251356 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 minutes, 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 to 188° C.

後処理

  1. temperatureto cool for 15 minutes
  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-2d7c93ac1a45444c992a3723849be3da
出典データセット
uspto-grants-2002_01
特許番号
US06342504B1

関連ノート

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