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

HRID 745436

반응식

HRID 745436 반응식
[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]

참가 물질

4

반응물 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 2290744-Methoxybenzenecarboximidamide

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-467a2c405e6b411cb6e2def6ef2ec4b7
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04598149

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