Ethyl 2-chloroacetoacetate → 5-chloro-6-methyl-1H-pyrimidin-4-one

HRID 745436

反応式

HRID 745436 の反応式
[Cl:1][CH:2]([C:8]([CH3:10])=O)[C:3](OCC)=[O:4].COC1C=CC([C:17]([NH2:19])=[NH:18])=CC=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:8]([CH3:10])=[N:18][CH:17]=[N:19][C:3]=1[OH:4]

参加物

4

反応物 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 2290744-Methoxybenzenecarboximidamide

生成物 1

HCID 1784332125-chloro-6-methyl-1H-pyrimidin-4-one収率 37.2%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

Under N2, a solution of ethyl 2-chloroacetoacetate (1.8 ml, d=1.15, 0.013 mol) in CHCl3 (50 ml) was added dropwise to a solution 4-methoxybenzamidine (3.9 g, 0.026 mol) in CHCl3 (100 ml). After stirring overnight, the reaction mixture was filtered and the filtrate was washed with dilute NaOH solution. The aqueous layer was extracted with CH2Cl2 (3×) and the organic layer was dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product was eluted with 2% CH3OH-CHCl3 (v/v) to yield 0.7 g (22%) of product m.p. 250°-251° C.

後処理

  1. filtrationthe reaction mixture was filtered
  2. washthe filtrate was washed with dilute NaOH solution
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  4. customthe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was chromatographed on silica gel
  8. washthe product was eluted with 2% CH3OH-CHCl3 (v/v)

出典と根拠

ORDレコード
ord-467a2c405e6b411cb6e2def6ef2ec4b7
出典データセット
uspto-grants-1986_07
特許番号
US04598149

関連ノート

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