Potassium Carbonate → 4-Amino-8-(1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethyl)pyrido[2,3-d]pyrimidin-5(8H)-one

HRID 634453Notes

Reaction equation

HRID 634453 reaction equation
Br[CH:2]([C:4]1[O:5][C:6](=[O:20])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].[NH2:21][C:22]1[C:23]2[C:31](=[O:32])[CH:30]=[CH:29][NH:28][C:24]=2[N:25]=[CH:26][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:21][C:22]1[C:23]2[C:31](=[O:32])[CH:30]=[CH:29][N:28]([CH:2]([C:4]3[O:5][C:6](=[O:20])[C:7]4[C:12]([C:13]=3[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH3:3])[C:24]=2[N:25]=[CH:26][N:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57067884-aminopyrido[2,3-d]pyrimidin-5(8H)-oneHCID 1181310753-(1-Bromoethyl)-4-phenyl-1H-isochromen-1-one2×

Product 1

HCID 1181311174-Amino-8-(1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethyl)pyrido[2,3-d]pyrimidin-5(8H)-oneYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1-Bromoethyl)-4-phenyl-1H-isochromen-1-one (intermediate C7, 50 mg, 0.15 mmol), 4-aminopyrido[2,3-d]pyrimidin-5(8H)-one (37 mg, 0.23 mmol), potassium carbonate (31.5 mg, 0.23 mmol) were reacted in DMF (0.5 ml) at 80° C. The crude was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound (32 mg, 51%).

Workup

  1. customThe crude was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%)

Sources & evidence

ORD record
ord-65a727c1601b48ab84a6e57bfbd67862
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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