Methanol → 3-[2-(Methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine

HRID 1159874Notes

Reaction equation

HRID 1159874 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:6]=[CH:5][N:4]=1.[I-].[NH2:21][N+:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[K+].CO>C(Cl)Cl.O>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)=[N:21][N:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=23)[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 595114132-(Methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine

Product 1

HCID 595114283-[2-(Methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

To a 0° C. solution of 2-(methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine (4.0 g, 14.7 mmol) and N-aminopyridinium iodide (6.53 g, 29.4 mmol) in DCM (150 mL) is added KOH (2.06 g, 36.8 mmol) in H2O (50 mL). The reaction is allowed to warm to rt and stirred for 16 h. The mixture is diluted with DCM and H2O. The organic layer is separated and the aqueous layer is extracted with DCM. The combined organic layers are dried over MgSO4, filtered and concentrated to give a dark solid. The residue is dissolved in DCM and MeOH is added until the product formed as a precipitate. The product is collected by filtration and dried to supply the title compound (2.02 g) as an off-white solid. 1H NMR (400 MHz, d6-DMSO): δ 11.36 (s, 1H), 8.62 (d, 1H, J=9.2), 8.54 (d, 1H, J=5.6), 7.94 (s, 1H), 7.82 (d, 1H, J=8.8), 7.54 (t, 1H, J=8.0), 7.46 (d, 1H, J=9.2), 7.16 (d, 1H, J=5.2), 2.59 (s, 3H).

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with DCM
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark solid
  7. customformed as a precipitate
  8. filtrationThe product is collected by filtration
  9. dry with materialdried to supply the title compound (2.02 g) as an off-white solid

Sources & evidence

ORD record
ord-12bfc42612004405b0231a3c75572015
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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