Toluene → 7-Chloro-5-methyl-3-(2-chloro-4-methylphenyl)pyrazolo[1,5-a]pyrimidine

HRID 10236

反応式

HRID 10236 の反応式
O[C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=3[Cl:18])=[C:6]2[N:5]=[C:4]([CH3:19])[CH:3]=1.P(Cl)(Cl)([Cl:22])=O.C(N(CC)C1C=CC=CC=1)C.C1(C)C=CC=CC=1>CCCCCC.CCOC(C)=O>[Cl:22][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=3[Cl:18])=[C:6]2[N:5]=[C:4]([CH3:19])[CH:3]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178418862HCID 178418862、化合物

生成物 1

HCID 219796097-Chloro-5-methyl-3-(2-chloro-4-methylphenyl)pyrazolo[1,5-a]pyrimidine収率 88%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 7-hydroxy-5-methyl-3-(2-chloro-4-methylphenyl)-pyrazolo[1,5-a]pyrimidine (1.0 g, 3.5 mmol), phosphorus oxychloride (2.7 g, 1.64 mL, 17.4 mmol), N,N-diethylaniline (0.63 g, 0.7 mL, 4.2 mmol) and toluene (20 mL) was stirred at reflux temperature for 3 hours, then it was cooled to ambient temperature. The volatiles were removed in vacuo. Flash chromatography (EtOAc:hexane::1:2) on the residue gave 7-chloro-5-methyl-3-(2-chloro-4-methylphenyl)pyrazolo[1,5-a]pyrimidine (900 mg, 84% yield) as a yellow oil: NMR (CDCl3, 300 Hz): 7.35 (s, 1H), 7.28–7.26 (m, 1H), 71.6 (d, 1H, J=7), 6.80 (s, 1H), 2.55 (s, 3H), 2.45 (s, 3H), 2.40 (s, 3H); CI-MS: 306 (M+H).

後処理

  1. temperatureat reflux temperature for 3 hours
  2. customThe volatiles were removed in vacuo

出典と根拠

ORDレコード
ord-f75ca00c8a2d4cd79176f32f013e8113
出典データセット
uspto-grants-2006_08
特許番号
US07094782B1

関連ノート

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