Triethylamine → 7-Chloro-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine

HRID 348008ノート

反応式

HRID 348008 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:18]=[C:11]2[N:12]=[C:13]([CH3:17])[CH:14]=[C:15](O)[N:10]2[N:9]=1.C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:28].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:28][C:15]1[N:10]2[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:18]=[C:11]2[N:12]=[C:13]([CH3:17])[CH:14]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178429159HCID 178429159、化合物

生成物 1

HCID 210837187-Chloro-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine収率 86%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

To a slurry of 2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-ol (I-1A-3f; 700 mg, 2.70 mmol) and triethylamine (0.57 ml, 4.0 mmol) in toluene (30 ml) at room temperature was added POCl3 (1.3 ml, 14 mmol), dropwise. The mixture was heated at 95° C. for 21 hours, cooled to room temperature, then slowly added to a stirred mixture of ice, saturated aqueous sodium bicarbonate and ethyl acetate. The aqueous layer was separated and extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and then concentrated, in vacuo, to afford the crude product (0.79 g). Purification on a Biotage™ Flash 40S column using 0–20% ethyl acetate in hexanes as eluant afforded I-1A-3g as an off-white solid (643 mg, 86%): +ESI MS (M+1) 278.12; 1H NMR (400 MHz, CD2Cl2) δ 7.96–7.93 (m, 1H), 7.54–7.51 (m, 1H), 7.50–7.35 (m, 2H), 7.15 (s, 1H), 6.90 (s, 1H), 2.59 (s, 3H).

後処理

  1. temperaturecooled to room temperature
  2. customThe aqueous layer was separated
  3. extractionextracted with additional ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated, in vacuo
  7. customto afford the crude product (0.79 g)
  8. customPurification on a Biotage™ Flash 40S column

出典と根拠

ORDレコード
ord-79ae36246ee447cca58a24f69a7bae81
出典データセット
uspto-grants-2007_02
特許番号
US07176210B2

反応ノート

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