Phosphorus oxychloride → 3-Benzenesulphonyl-7-chloro-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

HRID 636435

反応式

HRID 636435 の反応式
[C:1]1([S:7]([C:10]2[C:11]([S:23][CH3:24])=[N:12][N:13]3[C:18](O)=[CH:17][C:16]([CH2:20][O:21][CH3:22])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:27]>CCN(C1C=CC=CC=1)CC>[C:1]1([S:7]([C:10]2[C:11]([S:23][CH3:24])=[N:12][N:13]3[C:18]([Cl:27])=[CH:17][C:16]([CH2:20][O:21][CH3:22])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178494547HCID 178494547、化合物

生成物 1

HCID 212549933-Benzenesulphonyl-7-chloro-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine収率 79%

試薬・触媒・溶媒 1

HCID 7061N,N-Diethylaniline溶媒

実験手順

A suspension of 2.5 g (6.8 mmol) of 3-benzenesulphonyl-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol in 40 ml of POCl3 and 20 ml of diethylaniline was heated at reflux for 1 hr. The reaction solution was cooled to RT and evaporated. The residue was treated with 100 ml of ice-water and the pH value of the solution was adjusted to 8 with sat. NaHCO3 solution. The aqueous phase was extracted three times with 100 ml of CH2Cl2,and the organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 20:1) yielded 2.1 g (79%) of 3-benzenesulphonyl-7-chloro-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine as a pale yellow powder, m.p. 194-197°.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 1 hr
  3. customevaporated
  4. additionThe residue was treated with 100 ml of ice-water
  5. extractionThe aqueous phase was extracted three times with 100 ml of CH2Cl2,and the organic phases
  6. dry with materialwere dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-64ed753f56ed48a1a3bd9bd5c4f7ba90
出典データセット
uspto-grants-2001_02
特許番号
US06194410B1

関連ノート

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