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

HRID 383799

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[C:14]([NH2:15])=[CH:13][CH:12]=[N:11]1.[Na+].[I-].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][C:14]2[NH:10][N:11]=[CH:12][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-5-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 EtOAc. 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 pink 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-463b30d362164ec98a3e5b14858f956d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367690B2

Linked notes

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