N-bromobutanimide → (6-Bromo-3-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene)methylamine

HRID 1167143ノート

反応式

HRID 1167143 の反応式
[CH2:1]([N:4]1[C:9](=[CH:10][NH2:11])[C:8]2[CH:12]=[CH:13][S:14][C:7]=2[N:6]=[C:5]1[O:15][CH2:16][CH2:17][CH3:18])[CH2:2][CH3:3].[Br:19]N1C(=O)CCC1=O>N1C=CC=CC=1>[Br:19][C:13]1[S:14][C:7]2[N:6]=[C:5]([O:15][CH2:16][CH2:17][CH3:18])[N:4]([CH2:1][CH2:2][CH3:3])[C:9](=[CH:10][NH2:11])[C:8]=2[CH:12]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 69986416(3-Propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene)methylamine

生成物 1

HCID 53813426(6-Bromo-3-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene)methylamine

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

In a sulfonation flask, 1.2 g (0.0045 mol) (3-propyl-2-propoxy-3H-thieno[2,3-d]-pyrimidine-4-ylidene)methylamine are dissolved in 15 ml of absolute pyridine. Then the internal temperature is raised to 60° C. and 1.2 g (0.0068 mol) N-bromosuccinimide are added in three portions. After stirring for 3 hours at 60° C., the pyridine is distilled off in a water jet vacuum and the residue taken up in ethylacetate. The organic phase is washed three times with water and after drying the organic phase over Na2SO4 the solvent is removed in a water jet vacuum. The raw material is purified by column chromatography over silica gel (eluant: hexane/ethylacetate 3:1). Yield: 1.2 g of (6-bromo-3-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene)methylamine in the form of a brownish oil (1H-NMR-data see table 5).

後処理

  1. distillationthe pyridine is distilled off in a water jet vacuum
  2. washThe organic phase is washed three times with water
  3. dry with materialafter drying the organic phase over Na2SO4 the solvent
  4. customis removed in a water jet vacuum
  5. customThe raw material is purified by column chromatography over silica gel (eluant: hexane/ethylacetate 3:1)

出典と根拠

ORDレコード
ord-6c87a49ec6c3405fb0de550efd01e9a1
出典データセット
uspto-grants-2003_09
特許番号
US06617330B2

反応ノート

読み込み中…