Cesium carbonate → 3-(4-Methoxy-benzyl)-5-(4-quinoxalin-2-yl-phenoxy)-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one

HRID 1045508

Reaction equation

HRID 1045508 reaction equation
Cl[C:2]1[C:11]2[CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:8](=[O:21])[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][C:23]=1[C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:9]2[CH2:10][C:11]3[C:2]([O:38][C:35]4[CH:36]=[CH:37][C:32]([C:23]5[CH:24]=[N:25][C:26]6[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=6)[N:22]=5)=[CH:33][CH:34]=4)=[CH:3][CH:4]=[N:5][C:6]=3[NH:7][C:8]2=[O:21])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 7873664-Quinoxalin-2-ylphenolHCID 669262915-chloro-3-[(4-methoxyphenyl)methyl]-1H,2H,3H,4H-pyrido[2,3-d]pyrimidin-2-one

Product 1

HCID 704992413-(4-Methoxy-benzyl)-5-(4-quinoxalin-2-yl-phenoxy)-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-oneYield 42.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of 5-chloro-3-(4-methoxy-benzyl)-3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-2-one (100.00 mg; 0.33 mmol; 1.00 eq.), 4-quinoxalin-2-ylphenol (91.46 mg; 0.41 mmol; 1.25 eq.), and cesium carbonate (214.54 mg; 0.66 mmol; 2.00 eq.) in DMF (2.00 ml) was heated in a microwave at 130° C. for 4 hours. The reaction was concentrated, redissolved in DMSO, syringe filtered, and purified via prep HPLC to afford 69 mg of 280 as an off-white solid. LC-MS (M+H=490, obsd.=490).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in DMSO
  3. filtrationsyringe filtered
  4. custompurified via prep HPLC

Sources & evidence

ORD record
ord-e7b9b692cfe24bcb9cbc699769f3cb7a
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Linked notes

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