Sodium Carbonate → HCID 59242778, compound

HRID 1514419Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[CH3:10][C:11]1[C:16](B(O)O)=[CH:15][CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:10][C:11]1[C:16]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

Conditions

Temperature: 96 °C

Procedure

To a solution of 4-iodo-2-methylsulfanyl-pyrimidine (600 mg, 2.38 mmol), 2-methylpyridine-3-boronic acid (533 mg, 3.09 mmol), Na2CO3 (756 mg, 7.14 mmol), triphenylphosphine (62 mg, 0.24 mmol) in nPrOH (10 ml), Pd(OAc)2 (16 mg, 0.07 mmol) was added and the mixture was stirred at 96° C. for 1.5 hours. The solvent was evaporated under vacuum, and the crude was dissolved in DCM and washed with water. The organic phase was dried (Na2SO4) and evaporated. A second batch of this compound was prepared according to the same protocol starting from 0.45 mmol of 4-iodo-2-methylsulfanyl-pyrimidine. The residues, deriving from the two batches, were purified by flash chromatography with DCM-MeOH—NH4OH (20-0.1-0.2) to give 568 mg of the title compound (92% yield).

Workup

customThe solvent was evaporated under vacuum
dissolutionthe crude was dissolved in DCM
washwashed with water
dry with materialThe organic phase was dried (Na2SO4)
customevaporated
customA second batch of this compound was prepared
customwere purified by flash chromatography with DCM-MeOH—NH4OH (20-0.1-0.2)

Sources & evidence

ORD record: ord-19015cd65c0248e6b57f8a85b98b5a56
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222266B2

Reaction notes

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