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

HRID 452863Notes

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

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

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

Sources & evidence

ORD record: ord-d497ae6e0dd14991af9169bcfb0f9cac
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492397B2

Reaction notes

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