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

HRID 32345

반응식

HRID 32345 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-484b93adf97c48f698d4757d78117903
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427626B2

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