Sodium Iodide → HCID 178418729, compound

HRID 1013904Notes

Reaction equation

HRID 1013904 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[NH2:11][C:12]1[CH:16]=[C:15]([CH3:17])[NH:14][N:13]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>C(O)CCC>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:11][C:12]2[NH:13][N:14]=[C:15]([CH3:17])[CH:16]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-

Product 1

HCID 178418729HCID 178418729, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine (5 g, 25.6 mmol) and 3-amino-5-methylpyrazole 2.61 g, 26.9 mmol) in BuOH (60 mL) is added diisopropylethylamine (4.69 mL, 26.9 mmol) followed by sodium iodide (3.84 g, 25.6 mmol). The reaction mixture is stirred for 15 hours at 120° C. The solvent is then removed in vacuo and the residue is purified by flash chromatography (SiO2, hexane/AcOEt gradient) to give [6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine.

Workup

  1. customThe solvent is then removed in vacuo
  2. customthe residue is purified by flash chromatography (SiO2, hexane/AcOEt gradient)

Sources & evidence

ORD record
ord-e2d03311d0dd4b95814a6738adcb5751
Source dataset
uspto-grants-2011_07
Patent number
US07982037B2

Reaction notes

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