6-Methoxy-3-pyridinylamine → HCID 66600240、化合物

HRID 1621374ノート

反応式

HRID 1621374 の反応式
F[C:2]1[C:7]([C:8]2[N:16]=[CH:15][N:14]=[C:13]3[C:9]=2[N:10]=[CH:11][N:12]3[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:25]=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[CH3:31][O:30][C:27]1[N:26]=[CH:25][C:24]([NH:23][C:2]2[C:7]([C:8]3[N:16]=[CH:15][N:14]=[C:13]4[C:9]=3[N:10]=[CH:11][N:12]4[CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 811216-Methoxy-3-pyridinylamineHCID 2733832Lithium HexamethyldisilazideHCID 444791786-(2-Fluoropyridin-3-YL)-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

生成物 1

HCID 66600240HCID 66600240、化合物収率 71.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (196.6 mg, 657 μmol) and 3-amino-6-methoxypyridine (Aldrich, St. Louis, Mo.) (101.9 mg, 821 μmol) in THF (2.0 mL) was cooled in an ice bath and treated with LiHMDS (3.0 mL, 3.0 mmol). A blood-red solution was obtained. The mixture was stirred for 1 h, and then quenched with water (0.1 mL). The mixture was extracted into EtOAc from saturated aqueous NaHCO3, concentrated and purified by flash chromatography on silica (50% EtOAc/hexane; yellow band from column) to give 6-methoxy-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)pyridin-3-amine (190 mg, 71.7% yield) as a yellow crystalline solid. 1H NMR (400 MHz, CDCl3) δ 12.06 (s, 1H); 9.68 (dd, J=7.82, 1.76 Hz, 1H); 8.99 (s, 1H); 8.44 (d, J=2.54 Hz, 1H); 8.28 (dd, J=4.69, 1.76 Hz, 1H) 8.34 (s, 1H); 8.05 (dd, J=8.90, 2.64 Hz, 1H); 6.88 (dd, J=7.82, 4.69 Hz, 1H); 6.77 (d, J=8.80 Hz, 1H); 5.86 (dd, J=10.37, 2.35 Hz, 1H); 4.16-4.25 (m, 1H); 3.95 (s, 3H); 3.82 (s, 1H); 1.98-2.24 (m, 3H); 1.61-1.89 (m, 3H). m/z (ESI, +ve) 404.0 (M+H)+.

後処理

  1. customA blood-red solution was obtained
  2. customquenched with water (0.1 mL)
  3. extractionThe mixture was extracted into EtOAc from saturated aqueous NaHCO3
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica (50% EtOAc/hexane; yellow band from column)

出典と根拠

ORDレコード
ord-569ea81b55d6403fb506da67a1c97d8b
出典データセット
uspto-grants-2014_07
特許番号
US08772480B2

反応ノート

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