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

HRID 1897648Notes

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) was heated at 40° C. for 24 h. The solvent was removed in vacuo. The resulting residue was partitioned between EtOAc (350 mL) and water (100 mL). The EtOAc layer was washed with water (3×), saturated aqueous NaCl (1×), dried over Na2SO4, and concentrated in vacuo. The resulting crude product was sonicated in Et2O (200 mL) and the resulting precipitate collected by filtration. This powder was 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 was removed in vacuo
customThe resulting residue was partitioned between EtOAc (350 mL) and water (100 mL)
washThe EtOAc layer was washed with water (3×), saturated aqueous NaCl (1×)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe resulting crude product was sonicated in Et2O (200 mL)
filtrationthe resulting precipitate collected by filtration
washThis powder was further washed with Et2O

Sources & evidence

ORD record: ord-d7d270c8d8f949dc8cd235f6ba9094be
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519129B2

Reaction notes

Loading…