Cesium carbonate → HCID 86713604, compound

HRID 2404069Notes

Reaction equation

HRID 2404069 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:5]([CH3:21])=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][C:24]=1[N+:32]([O-:34])=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(O)(C)C.CCOC(C)=O.CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.[Pd]>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:6]2[C:5]([CH3:21])=[CH:4][N:3]=[C:2]([NH:22][C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][C:24]=3[N+:32]([O-:34])=[O:33])[N:7]=2)[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 86713603HCID 86713603, compound

Product 1

HCID 86713604HCID 86713604, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 90416887HCID 90416887, compoundCatalystHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 4-(2-chloro-5-methylpyrimidin-4-yl)piperazine-1-carboxylate (0.15 g, 0.48 mmol), 4-amino-3-nitrobenzoic acid (97 mg, 0.53 mmol), BrettPhos-Pd Admixture (20 mg, 0.015 mmol), and cesium carbonate (470 mg, 1.44 mmol) in tBuOH (2.4 mL) was heated in a sealed tube at 100° C. overnight. The mixture was diluted with EtOAc, filtered through a celite plug, loaded onto silica gel and purified using 0-10% MeOH/DCM gradient to give the title compound (75 mg, 34%). MS (ES+) C21H26N6O6 requires: 458. found: 459 [M+H]+

Workup

  1. filtrationfiltered through a celite plug
  2. custompurified

Sources & evidence

ORD record
ord-a642bdf45ad642428ea1412c5f745dc5
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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