N-Methylbenzeneethanamine → 2-(N-methylphenethylamino)-6-phenylpyrimidine-4-carboxamide

HRID 68299

반응식

HRID 68299 반응식
CS([C:5]1[N:10]=[C:9]([C:11]([NH2:13])=[O:12])[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1)(=O)=O.CCN(C(C)C)C(C)C.[CH3:29][NH:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCOCC1>[CH3:29][N:30]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:5]1[N:10]=[C:9]([C:11]([NH2:13])=[O:12])[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1

참가 물질

5

반응물 3

HCID 11503N-MethylbenzeneethanamineHCID 81531DiisopropylethylamineHCID 58872694HCID 58872694, 화합물

생성물 1

HCID 156035462-(N-methylphenethylamino)-6-phenylpyrimidine-4-carboxamide수율 51.7%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

2-Methanesulfonyl-6-phenylpyrimidine-4-carboxamide (70 mg, 0.25 mmol), 1,4-dioxane (4 mL), DIPEA (0.3 mL, 2.0 mmol) and N-methylphenethylamine (82 mg, 0.6 mmol) were added to a 8 mL vial. The vial was sealed and heated at 85° C. for two days. The reaction mixture was allowed to cool to room temperature, and the solvent then removed by centrifugal evaporation. The residue was purified by preparative HPLC to afford 43 mg of 2-(N-methylphenethylamino)-6-phenylpyrimidine-4-carboxamide. 1H NMR (CDCl3, 300 MHz) δ 8.14 (m, 2H), 7.74 (s, 1H), 7.67 (br s, 1H), 7.47 (m, 3H), 7.25 (m, 5H), 5.79 (br s, 1H), 3.95 (t, J=6.9 Hz, 2H), 3.21 (s, 3H), 2.97 (t, J=6.9 Hz, 2H). HPLC ret. time 3.25 min, 10-100% CH3CN, 5 min run. ESI-MS m/z 333.3 (M+H)+.

후처리

  1. customThe vial was sealed
  2. temperatureto cool to room temperature
  3. customthe solvent then removed by centrifugal evaporation
  4. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-0539cb802972482dbf0f1709587fadb3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822451B2

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