Pyridinium, 1-amino-, iodide (1:1) → 2,3-Bis[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine

HRID 1269039ノート

反応式

HRID 1269039 の反応式
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)[CH:6]=[CH:5][N:4]=1.[I-].[NH2:20][N+:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][N:21]3[N:20]=2)[CH:6]=[CH:5][N:4]=1

参加物

4

反応物 2

HCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 184466152-(Methylsulfanyl)-4-{[2-(methylsulfanyl)-4-pyrimidinyl]ethynyl}pyrimidine

生成物 1

HCID 184466042,3-Bis[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine収率 71%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2-(Methylsulfanyl)-4-{[2-(methylsulfanyl)-4-pyrimidinyl]ethynyl}pyrimidine (0.1 g, 0.37 mmol) was dissolved in acetonitrile (5 mL). To this solution was added 1-aminopyridinium iodide (81 mg, 0.37 mmol) and 1,8-diazobicyclo[5.4.0]undec-7-ene (0.056 mL, 0.37 mmol) and the resulting mixture was stirred at room temperature overnight The resulting reddish suspension was concentrated in vacuo. Ethyl acetate and water were added to this residue. The phases were separated and the aqueous phase extracted with additional ethyl acetate. The organics were combined, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (1:1 ethyl acetate:hexane) gave 95 mg (71%) of 2,3-bis[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine as a solid. 1H NMR (CDCl3): δ 8.64 (d, 1H), 8.53 (d, 1H), 8.41 (d, 1H), 8.31 (d, 1H), 7.56 (d, 1H), 7.37 (t, 1H), 7.13 (d, 1H), 7.00 (t, 1H), 2.59 (s, 3H), 2.37 (s, 3H); MS m/z 367 (M+1).

後処理

  1. concentrationwas concentrated in vacuo
  2. additionEthyl acetate and water were added to this residue
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted with additional ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (1:1 ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-a56201ad54a84a1f890a7e97c19fd2e8
出典データセット
uspto-grants-2007_04
特許番号
US07199120B2

反応ノート

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