Sodium Iodide → 2-chloro-6-methyl-N-(1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 2383508Notes

Reaction equation

HRID 2383508 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[CH:14]=[CH:13][C:12]([NH2:15])=[N:11]1.[Na+].[I-].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CCOCC>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][C:12]2[NH:11][N:10]=[CH:14][CH:13]=2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 794712,4-Dichloro-6-methylpyrimidineHCID 81531DiisopropylethylamineHCID 178418806HCID 178418806, compound

Product 1

HCID 580550402-chloro-6-methyl-N-(1H-pyrazol-3-yl)pyrimidin-4-amineYield 78.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To the solution of 2,4-dichloro-6-methylpyrimidine (3.00 g) and 1H-pyrazol-3-amine (1.31 g) in NMP (30 mL) was added NaI (2.36 g) and DIEA (6.33 mL). And the mixture was heated to 80° C. under stirring. After 1 day, the mixture was cooled to room temperature. The mixture was diluted with Et2O. The precipitate was collected by filtration, washed with the mixed solvent of hexane and EtOAc and dried in vacuo to give 2-chloro-6-methyl-N-(1H-pyrazol-5-yl)pyrimidin-4-amine (2.60 g) as a pale yellow solid.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with the mixed solvent of hexane and EtOAc
  4. customdried in vacuo

Sources & evidence

ORD record
ord-eb2ebfb76f194d14b6d1bf7c039fab7b
Source dataset
uspto-grants-2012_09
Patent number
US08263632B2

Reaction notes

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