Sodium Carbonate → 2-chloro-5-methyl-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 2091927Notes

Reaction equation

[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[Cl:8][C:9]1[N:14]=[C:13](Cl)[C:12]([CH3:16])=[CH:11][N:10]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO>[Cl:8][C:9]1[N:14]=[C:13]([NH:7][C:4]2[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=2)[C:12]([CH3:16])=[CH:11][N:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 5-methyl-1H-pyrazol-3-amine (3.00 g, 30.9 mmol), 2,4-dichloro-5-methylpyrimidine (5.03 g, 30.9 mmol, 1 equiv.) and Na2CO3 (3.60 g, 34.0 mmol, 1.1 equiv.) in EtOH (100 mL) is heated at 40° C. for 24 h. The solvent is removed in vacuo. The resulting residue is partitioned between EtOAc (350 mL) and water (100 mL). The EtOAc layer is washed with water (3×), saturated aqueous NaCl (1×), dried over Na2SO4, and concentrated in vacuo. The resulting crude product is sonicated in Et2O (200 mL) and the resulting precipitate collected by filtration. This powder is further washed with Et2O, providing the product 2-chloro-5-methyl-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine; ESMS m/z 224.1 (M+H+).

Workup

customThe solvent is removed in vacuo
customThe resulting residue is partitioned between EtOAc (350 mL) and water (100 mL)
washThe EtOAc layer is washed with water (3×), saturated aqueous NaCl (1×)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe resulting crude product is sonicated in Et2O (200 mL)
filtrationthe resulting precipitate collected by filtration
washThis powder is further washed with Et2O

Sources & evidence

ORD record: ord-6fdc81e08c5f460f9f4ae9550ac2491c
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440681B2

Reaction notes

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