N-Methoxy-N-methylbenzamide → 2-Anilino4(2-benzoyl-1-isopropylimidazol-5-yl)pyrimidine

HRID 32345

反応式

HRID 32345 の反応式
C([Li])CCC.[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH:24]([CH3:26])[CH3:25])[C:22]([CH:27]=[O:28])=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CON(C)C(=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH:24]([CH3:25])[CH3:26])[C:22]([C:27](=[O:28])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 569575N-Methoxy-N-methylbenzamideHCID 116381022-Anilino4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 113949762-Anilino4(2-benzoyl-1-isopropylimidazol-5-yl)pyrimidine収率 43%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

n-Butyllithium (3.12 ml of 1.6 M solution in hexane, 5.0 mmol) was added to a stirred solution of 2-anilino-4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine (Example 10; 558 mg, 2.0 mmol) in anhydrous THF (20 ml) cooled to −70° C. The mixture was stirred for 30 minutes and then N-methoxy-N-methylbenzamide (660 mg, 4.0 mmol) was added and the reaction mixture was allowed to warm and stirred at ambient temperature for 18 hour. The reaction mixture was quenched with water (20 ml), and extracted with EtOAc (4×25 ml). The organic extracts were washed with brine (2×50 ml), dried and the volatiles removed by evaporation and the residue triturated with ether and the solid collected by filtration to give the title compound (303 mg, 43%) as a pale yellow crystalline solid. NMR (CDCl3): 1.55-1.70 (m, 8H), 5.52-5.68 (sept, 1H), 6.99 (d, 1H), 7.09 (dt, 1H), 7.18 (br s, 1H), 7.30-7.40 (m, 2H), 7.45-7.54 (m, 2H), 7.55 (s, 1H), 7.56-7.62 (m, 3H), 8.09 (d, 2H), 8.49 (d, 1 H); m/z 384.

後処理

  1. temperatureto warm
  2. stirringstirred at ambient temperature for 18 hour
  3. customThe reaction mixture was quenched with water (20 ml)
  4. extractionextracted with EtOAc (4×25 ml)
  5. washThe organic extracts were washed with brine (2×50 ml)
  6. customdried
  7. customthe volatiles removed by evaporation
  8. customthe residue triturated with ether
  9. filtrationthe solid collected by filtration

出典と根拠

ORDレコード
ord-484b93adf97c48f698d4757d78117903
出典データセット
uspto-grants-2008_09
特許番号
US07427626B2

関連ノート

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