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

HRID 1269039Notes

Reaction equation

HRID 1269039 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a56201ad54a84a1f890a7e97c19fd2e8
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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