Diethyl ethylmalonate → 5-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone

HRID 1443

反応式

HRID 1443 の反応式
O.Cl.[C:3]([NH2:11])(=[NH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C[O-].[Na+].[CH2:15]([CH:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19])[CH3:16]>CO>[CH2:15]([C:17]1[C:18](=[O:19])[NH:10][C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:11][C:23]=1[OH:24])[CH3:16]

参加物

5

反応物 3

HCID 8610Diethyl ethylmalonateHCID 10942334Sodium MethoxideHCID 16219042Benzamidine HCl hydrate

生成物 1

HCID 196906695-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone収率 51%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A mixture of 45.19 g (0.29 mol) of benzamidine hydrochloride hydrate, 127.42 g (0.59 mol) of 25% sodium methoxide in methanol, 55 mL (0.29 mol) of diethyl ethylmalonate and 175 mL of methanol was heated at reflux for 25 h. The mixture was rotovapped to remove the bulk of the methanol. The residue was diluted with 300 mL of water and the pH was adjusted to 7 with concentrated hydrochloric acid. The solid precipitate was collected by filtration and dried under vacuum at 50° C. to afford 31.89 g (51%) of crude 5-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone as a pale yellow solid. 1H-NMR (d6-DMSO) δ 1.05(3H,t), 2.39(2H,q), 7.5(3H,m), 8.1(2H,m).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 25 h
  3. customto remove the bulk of the methanol
  4. additionThe residue was diluted with 300 mL of water
  5. filtrationThe solid precipitate was collected by filtration
  6. customdried under vacuum at 50° C.

出典と根拠

ORDレコード
ord-28a790364d3a4b39a6924f5c3d8fb5d8
出典データセット
uspto-grants-1998_03
特許番号
US05726124

関連ノート

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