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

HRID 68299

反応式

HRID 68299 の反応式
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

参加物

5

反応物 3

HCID 11503N-MethylbenzeneethanamineHCID 81531DiisopropylethylamineHCID 58872694HCID 58872694、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-0539cb802972482dbf0f1709587fadb3
出典データセット
uspto-grants-2014_09
特許番号
US08822451B2

関連ノート

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