Potassium Carbonate → 6-(5-(Aminomethyl)-2-fluorophenyl)-8-cyclopentyl-4-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 2389970Notes

Reaction equation

[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:17][CH3:18])[N:14]=[C:15]([CH3:16])[C:10]=3[CH:9]=[C:8](B(O)O)[C:7]2=[O:22])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Br[C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[F:33])[CH2:28][NH2:29].C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:29][CH2:28][C:27]1[CH:26]=[CH:25][C:32]([F:33])=[C:31]([C:8]2[C:7](=[O:22])[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:11]3[N:12]=[C:13]([NH:17][CH3:18])[N:14]=[C:15]([CH3:16])[C:10]=3[CH:9]=2)[CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 8-cyclopentyl-4-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-ylboronic acid (30 mg, 0.099 mmol), 3-bromo-4-fluorobenzylamine hydrochloride (28.7 mg, 0.119 mmol), potassium carbonate (3 M, 0.10 mL) in DME (0.5 mL) and EtOH (0.5 mL) was added tetrakis(triphenylphosphine) palladium(0) (6 mg, 0.005 mmol). The mixture was degassed with N2, sealed and heated for 1 h at 100° C. in microwave. The mixture was removed under reduced pressure. The crude product was purified by chromatography to give the title compound (16.4 mg, 43.3%).

Workup

customThe mixture was degassed with N2
customsealed
customThe mixture was removed under reduced pressure
customThe crude product was purified by chromatography

Sources & evidence

ORD record: ord-c41ff8b5483b47b297e1d2df5a505de1
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273755B2

Reaction notes

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