Sodium Iodide → HCID 178418729, compound

HRID 1611632Notes

Reaction equation

HRID 1611632 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-821cd302656d48b9b86ce4f15e96cd78
Source dataset
uspto-grants-2006_01
Patent number
US06989385B2

Reaction notes

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