Potassium Carbonate → HCID 86713567, compound

HRID 524039Notes

Reaction equation

Br[C:2]1[CH:12]=[N:11][C:5]2[N:6]=[C:7]([NH2:10])[N:8]=[CH:9][C:4]=2[CH:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:2]2[CH:12]=[N:11][C:5]3[N:6]=[C:7]([NH2:10])[N:8]=[CH:9][C:4]=3[CH:3]=2)[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-bromopyrido[2,3-d]pyrimidin-2-amine (1.0 g, 4.46 mmol), 3,5-dimethoxyphenylboronic acid (1.2 g, 6.70 mmol), PdCl2(dppf) (364 mg, 0.446 mmol) and potassium carbonate (1.8 g, 13.39 mmol) in 1,4-dioxane/water (4 mL/1 mL) was degassed with nitrogen for 5 min and stirred at 110° C. for 30 min under microwave. The reaction mixture was cooled to RT, and concentrated to afford a crude product, which was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1) to afford 6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-amine as a yellow solid (400 mg, 31%). MS (ES+) C15H14N4O2 requires: 282. found: 283 [M+H]+.

Workup

customwas degassed with nitrogen for 5 min
temperatureThe reaction mixture was cooled to RT
concentrationconcentrated
customto afford a crude product, which
customwas purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1)

Sources & evidence

ORD record: ord-0941755d30d04558972885a60183c7a4
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340514B2

Reaction notes

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