Sodium hydride → Methyl 6-chloro-3-(2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)-2-methylbenzoate

HRID 650907노트

반응식

HRID 650907 반응식
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([N:13]=[C:14]=[O:15])=[CH:4][CH:3]=1.[H-].[Na+].[NH2:18][C:19]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:21]([O-])=[O:22]>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([N:13]2[C:21](=[O:22])[CH:20]=[C:19]([C:24]([F:27])([F:26])[F:25])[NH:18][C:14]2=[O:15])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 21710153Methyl 6-chloro-3-isocyanato-2-methylbenzoateHCID 734469833-Amino-4,4,4-trifluoro-2-butenoate

생성물 1

HCID 21710140Methyl 6-chloro-3-(2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)-2-methylbenzoate수율 58.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

This compound was prepared in a manner analogous to the second part of Step D, Example 1. Here, 16.7 grams (0.074 mole) of methyl 6-chloro-3-isocyanato-2-methylbenzoate was combined with 4.4 grams (0.110 mole) of 60% sodium hydride and 14.2 grams (0.076 mole) of 3-amino-4,4,4-trifluoro-2-butenoate in 600 mL of THF. The reaction product was purified by column chromatography on silica using a 1:1 mixture of EtOAc and hexane as eluant. The fractions containing product were combined and concentrated under reduced pressure, yielding 15.8 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

후처리

  1. customThis compound was prepared in a manner analogous to the second part of Step D, Example 1
  2. customThe reaction product was purified by column chromatography on silica using
  3. additiona 1:1 mixture of EtOAc and hexane as eluant
  4. additionThe fractions containing product
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-16ad04a994b54b608241912aceb911c0
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06277847B1

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