Cesium carbonate → HCID 66959852, compound

HRID 1023309Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH2:14][C:15]1[C:24]2[C:23](=[O:25])[N:22]([CH3:26])[CH:21]=[N:20][C:19]=2[CH:18]=[C:17]([C:27]2[CH:28]=[N:29][C:30]([C:33]([OH:36])([CH3:35])[CH3:34])=[CH:31][CH:32]=2)[N:16]=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:36][C:33]([C:30]1[N:29]=[CH:28][C:27]([C:17]2[N:16]=[C:15]([NH:14][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[C:24]3[C:23](=[O:25])[N:22]([CH3:26])[CH:21]=[N:20][C:19]=3[CH:18]=2)=[CH:32][CH:31]=1)([CH3:34])[CH3:35]

Participants

Conditions

Temperature: 85 °C

Procedure

2-iodopyridine (7.51 μL, 0.071 mmol), Cs2CO3 (41.9 mg, 0.129 mmol), and a catalytic amount of Pd(OAc)2 and xant phos ligand were added to a solution of 5-amino-7-(6-(2-hydroxypropan-2-yl)pyridin-3-yl)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (20.0 mg, 0.064 mmol) in anhydrous THF (0.5 mL). The reaction mixture was purged with N2 and heated at 85° C. overnight. The mixture was then cooled, quenched with H2O (5 mL) and extracted with ethyl acetate (3×2.5 mL). The combined organic layers were evaporated under vacuo and the residue was purified by preparatory LC/MS to provide the title compound; HPLC-MS calculated for C21H20N6O2 (M+H+) 389.2, found 389.2.

Workup

customThe reaction mixture was purged with N2
temperatureThe mixture was then cooled
customquenched with H2O (5 mL)
extractionextracted with ethyl acetate (3×2.5 mL)
customThe combined organic layers were evaporated under vacuo
customthe residue was purified by preparatory LC/MS

Sources & evidence

ORD record: ord-bb278d499c6f45649c95ee2483c3732d
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722692B2

Reaction notes

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