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

HRID 650907ノート

反応式

HRID 650907 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-16ad04a994b54b608241912aceb911c0
出典データセット
uspto-grants-2001_08
特許番号
US06277847B1

反応ノート

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