Sodium hydride → 2-n-butyl-6-chloro-3-n-propyl-3H-thieno[2,3-d]pyrimidine-4-one

HRID 650934ノート

反応式

HRID 650934 の反応式
[H-].[Na+].[CH2:3]([NH:6][C:7]([C:9]1[CH:13]=[C:12]([Cl:14])[S:11][C:10]=1[N:15]=[C:16]([CH2:19][CH2:20][CH2:21][CH3:22])OC)=[O:8])[CH2:4][CH3:5]>C1COCC1>[CH2:19]([C:16]1[N:6]([CH2:3][CH2:4][CH3:5])[C:7](=[O:8])[C:9]2[CH:13]=[C:12]([Cl:14])[S:11][C:10]=2[N:15]=1)[CH2:20][CH2:21][CH3:22]

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 542514365-Chloro-2-(1-n-butyl-1-methoxymethyleneamino)thiophene-3-carboxylic-acid propylamide

生成物 1

HCID 110334152-n-butyl-6-chloro-3-n-propyl-3H-thieno[2,3-d]pyrimidine-4-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In a sulfonation flask, 0.36 g of 5-Chloro-2-(1-n-butyl-1-methoxymethyleneamino)thiophene-3-carboxylic-acid propylamide is dissolved in 20 ml of absolute THF and 0.085 g of a ca. 55% NaH dispersion is added in one portion. The mixture is stirred for 15 minutes at room temperature and 1 hour at reflux temperature. Then the solvent is removed in a water jet vacuum and the residue taken up in ethylacetate. The organic phase is washed twice with water and after drylng of the organic phase with sodium sulfate, the solvent is removed in a water jet vacuum. The resulting crude product is purified by column chromatography over silica gel (eluant:hexane/ethylacetate=5:1). Yield: 0.2 g 2-n-butyl-6-chloro-3-n-propyl-3H-thieno[2,3-d]pynimidin-4-one in the form of a slightly yellowish powder; m.p. 67-69° C.

後処理

  1. temperatureat reflux temperature
  2. customThen the solvent is removed in a water jet vacuum
  3. washThe organic phase is washed twice with water
  4. customafter drylng of the organic phase with sodium sulfate, the solvent is removed in a water jet vacuum
  5. customThe resulting crude product is purified by column chromatography over silica gel (eluant:hexane/ethylacetate=5:1)

出典と根拠

ORDレコード
ord-26b059e7bd5c47b6a77fa1e58063ce40
出典データセット
uspto-grants-2001_08
特許番号
US06277858B1

反応ノート

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