Potassium Carbonate → 4-Chloro-6-((6-iodo-2-methylpyridin-3-yl)oxy)pyrimidine

HRID 718201Notes

Reaction equation

[I:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Cl:10][C:11]1[CH:16]=[C:15]([O:9][C:5]2[C:6]([CH3:8])=[N:7][C:2]([I:1])=[CH:3][CH:4]=2)[N:14]=[CH:13][N:12]=1

Participants

Conditions

Temperature: 110 °C

Procedure

6-Iodo-2-methylpyridin-3-ol (2.00 g, 8.51 mmol) and 4,6-dichloropyrimidine (5.00 g, 33.6 mmol) were dissolved in DMA (40 mL) and sonicated and sparged with Ar for 10 min. K2CO3 (2.00 g, 14.5 mmol) was added and the reaction mixture was stirred at 110° C. for 16 h. The mixture was partitioned between water (260 mL) and EtOAc (100 mL). The solids were removed by filtration through a pad of diatomaceous earth. The filter cake was washed with EtOAc (3×25 mL). The organic phase was collected and the aqueous phase was extracted with EtOAc (3×50 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo to afford 4-chloro-6-((6-iodo-2-methylpyridin-3-yl)oxy)pyrimidine (2.8 g, 95%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 8.63 (s, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.57 (s, 1H), 7.41 (d, J=8.3 Hz, 1H), 2.25 (s, 3H). MS (ESI) m/z: 348.0 (M+H+).

Workup

customsonicated
customsparged with Ar for 10 min
customThe mixture was partitioned between water (260 mL) and EtOAc (100 mL)
customThe solids were removed by filtration through a pad of diatomaceous earth
washThe filter cake was washed with EtOAc (3×25 mL)
customThe organic phase was collected
extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
dry with materialThe combined organics were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ef74ae39459a4a8eabbce9f610c1b206
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193719B2

Reaction notes

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