Cesium carbonate → 5-[(3-amino-1-methyl-1H-indazol-6-yl)oxy]-3-(4-methoxybenzyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

HRID 1045504

Reaction equation

HRID 1045504 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.[NH2:22][C:23]1[C:31]2[C:26](=[CH:27][C:28]([OH:32])=[CH:29][CH:30]=2)[N:25]([CH3:33])[N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[NH2:22][C:23]1[C:31]2[C:26](=[CH:27][C:28]([O:32][C:2]3[C:11]4[CH2:10][N:9]([CH2:12][C:13]5[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=5)[C:8](=[O:21])[NH:7][C:6]=4[N:5]=[CH:4][CH:3]=3)=[CH:29][CH:30]=2)[N:25]([CH3:33])[N:24]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 669262911265634-73-8HCID 1357424603-amino-1-methyl-1H-indazol-6-ol

Product 1

HCID 704971855-[(3-amino-1-methyl-1H-indazol-6-yl)oxy]-3-(4-methoxybenzyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-oneYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Suspended 5-chloro-3-(4-methoxy-benzyl)-3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-2-one (400.00 mg; 1.32 mmol; 1.00 eq.), 3-amino-1-methyl-1h-indazol-6-ol (268.61 mg; 1.65 mmol; 1.25 eq.) and cesium carbonate (858.15 mg; 2.63 mmol; 2.00 eq.) in DMF (4.00 ml). Heated in a microwave at 130° C. for 90 min. The reaction was concentrated, redissolved in DMSO (20 mL) and filtered through celite. Purified filtrate via prep HPLC to afford 400 mg (56%) of compound 276 as a tan solid. LC-MS (M+H=431, obsd.=431)

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in DMSO (20 mL)
  3. filtrationfiltered through celite

Sources & evidence

ORD record
ord-ca4ffde5bd114f9091d795fa9afd8acc
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Linked notes

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