Hydrochloric Acid → HCID 11587369, compound

HRID 628828Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=2)[N:5]=[CH:4][N:3]=1.[C:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([OH:17])=[O:16].C([O-])([O-])=O.[Na+].[Na+].Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:10]1([CH3:14])[CH:11]=[CH:12][CH:13]=[C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([C:21]3[CH:22]=[CH:23][C:18]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=3)[CH:7]=2)[CH:9]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Part B. A 10 mL microwave tube is charged with 4-chloro-6-m-tolyl-pyrimidine (45.7 mg, 0.22 mmol), 4-carboxyphenylboronic acid (39.2 mg, 0.23 mmol), (235.3 mg, 2.22 mmol), Na2CO3 (70.6 mg, 0.67 mmol), tetrabutylammonium iodide (83.0 mg, 0.22 mmol), palladium acetate (0.5 mg, 2.2×mmol) and 2 mL of water. The reaction mixture is heated to 150° C. at 60 w, 250 psi in a microwave reactor for 10 min. The reaction mixture is added to 5 mLl of 6 N HCl and extracted with ethyl acetate (10 mL). The organic portion is washed with saturated NaHCO3 and brine, dried (MgSO4), and concentrated on a rotary evaporator. The oily residue is suspended in ethyl acetate/hexanes (1:1) to provide 9.8 mg (15.1% yield) of white powder as the desired product, m.p. 211-213° C. 1H NMR (300 MHz, DMSO-d6): δ 9.31 (1H, s), 8.66 (1H, s), 8.46 (2H, d, J=8.3 Hz), 8.20 (1H, s), 8.15 (1H, dd, J=8.0, 1.2 Hz), 8.09 (2H, d, J=8.3 Hz), 7.45 (1H, t, J=7.7 Hz), 7.38 (111, dd, J=7.7, 1.0 Hz). MS (ES+): m/e 291.58.

Workup

extractionextracted with ethyl acetate (10 mL)
washThe organic portion is washed with saturated NaHCO3 and brine
dry with materialdried (MgSO4)
concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record: ord-2f19311c4e50430abdf50d0ffe09e4ea
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315467B2

Reaction notes

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