2-Aminopyridine → 2,4-Disubstituted Pyrimidine 4a

HRID 968249ノート

反応式

HRID 968249 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].CS([C:14]1[N:19]=[C:18]([N:20]2[CH:24]=[CH:23][N:22]=[C:21]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:17]=[CH:16][N:15]=1)(=O)=O>C1COCC1>[C:25]1([C:21]2[N:20]([C:18]3[CH:17]=[CH:16][N:15]=[C:14]([NH:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=4)[N:19]=3)[CH:24]=[CH:23][N:22]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

参加物

5

反応物 3

HCID 104392-AminopyridineHCID 24758Sodium hydrideHCID 22288411HCID 22288411、化合物

生成物 1

HCID 53294302,4-Disubstituted Pyrimidine 4a

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-aminopyridine (31 mg, 0.33 mmol) in dry THF (0.5 mL) was added NaH (32 mg, 1.33 mmol) at room temperature. Once the resulting bubbling had ceased, 2-(methylsulfonyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (0.100 g, 0.33 mmol) was added all at once. After 1.5 hours the mixture was concentrated in vacuo, diluted with water and the pH of the resulting solution was adjusted to 7 with 1M HCl (aq). The resulting precipitate was filtered and purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA). 1H-NMR (300 MHz, CDCl3) δ 8.44 (d overlapping with s, J=5.4 Hz, 2H), 8.33 (d, J=4.1 Hz, 1H), 7.93 (d, J=8.3 Hz, 1H), 7.55 (m, 4H), 7.40 (m, 3H), 7.33 (m, 1H), 6.95 (dd, J=4.9, 7.1 Hz, 1H), 6.45 (d, J=5.3 Hz, 1H).

後処理

  1. customOnce the resulting bubbling
  2. concentrationAfter 1.5 hours the mixture was concentrated in vacuo
  3. additiondiluted with water
  4. filtrationThe resulting precipitate was filtered
  5. custompurified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA)

出典と根拠

ORDレコード
ord-2b6dfdd04cfb4d87a3148b9da5e0c9ba
出典データセット
uspto-grants-2005_10
特許番号
US06958340B2

反応ノート

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