Dimethyl Sulfoxide → 6-Ethoxy-2-phenylpyrimidin-4(3H)-one

HRID 1444

反応式

HRID 1444 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-])(=O)C.[Na+].[CH2:17]([O:19][C:20](OCC)=[CH:21][C:22](OCC)=[O:23])[CH3:18].CS(C)=O>[OH-].[Na+]>[CH2:17]([O:19][C:20]1[N:11]=[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:10][C:22](=[O:23])[CH:21]=1)[CH3:18]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 1693882-Propenoic acid, 3,3-diethoxy-, ethyl esterHCID 517045Sodium AcetateHCID 16219042Benzamidine HCl hydrate

生成物 1

HCID 6084316-Ethoxy-2-phenylpyrimidin-4(3H)-one収率 57%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 3.14 g (20.0 mmol) of benzamidine hydrochloride hydrate, 1.65 g (20.1 mmol) of powdered anhydrous sodium acetate, 4.17 g (22.2 mmol) of ethyl 3,3-diethoxyacrylate and 10 mL of DMSO was heated at 120° C. for 8 h. The mixture was cooled, diluted with 50 mL of 5% aqueous NaOH and washed with two 100 mL portions of ether. The aqueous layer was acidified with concentrated hydrochloric acid and the precipitate was collected by filtration and dried under vacuum at 50° C. to furnish 2.28 g (57%) of crude 6-ethoxy-2-phenyl-4(3H)-pyrimidinone as a yellow solid 1 H-NMR (d6-DMSO) δ 1.35(3H,t), 4.33(2H,q), 5.60(1H,s), 7.50(3H,m), 8.2(2H,m).

後処理

  1. temperatureThe mixture was cooled
  2. washwashed with two 100 mL portions of ether
  3. filtrationthe precipitate was collected by filtration
  4. customdried under vacuum at 50° C.

出典と根拠

ORDレコード
ord-2b0378d7412b4bedb3ed0ed2242b2a38
出典データセット
uspto-grants-1998_03
特許番号
US05726124

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