Sodium Iodide → HCID 86638335, compound

HRID 386592Notes

Reaction equation

HRID 386592 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.C(N(CC)C(C)C)(C)C.[I-].[Na+].[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[C:22]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[N:21]=1>CN(C=O)C>[Cl:19][C:20]1[N:21]=[C:22]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[N:23]=[C:24]([NH:7][C:4]2[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=2)[CH:25]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 59158122HCID 59158122, compound

Product 1

HCID 86638335HCID 86638335, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture containing 5-methyl-1H-pyrazol-3-amine 187 mg, 1.93 mmol), N,N-diisopropylethylamine (503 μl, 2.89 mmol), sodium iodide (289 mg, 1.93 mmol) and DMF (50 mL) was treated with 4,6-dichloro-2-(2-chlorophenyl)pyrimidine (500 mg, 1.93 mmol). The reaction mixture was then heated at 110° C. for 48 h before being cooled to room temperature and concentrated in vacuo. The resulting residue was purified by column chromatography (eluting with MeOH/DCM, 5/95) to give the title compound as a solid (433 mg, 70%). MS (ES+) m/e=320. 1H NMR: (DMSO) 2.18-2.23 (3H, m), 7.40-7.70 (6H, m), 10.32 (1H, s), 12.10 (1H, brs)

Workup

  1. temperaturebefore being cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by column chromatography (eluting with MeOH/DCM, 5/95)

Sources & evidence

ORD record
ord-c75fa93ca5a84f44a4c6dc1c98926c48
Source dataset
uspto-grants-2013_02
Patent number
US08372850B2

Reaction notes

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