Cesium carbonate → HCID 58071454, compound

HRID 1256043Notes

Reaction equation

HRID 1256043 reaction equation
[Br:1][C:2]1[C:3]([C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32](S(C3C=CC(C)=CC=3)(=O)=O)[CH:31]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)[CH2:17][CH2:16]3)=[CH:11][C:10]=2[O:28][CH3:29])=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CO.C1COCC1>[Br:1][C:2]1[C:3]([C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][CH:31]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:16][CH2:17][CH:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)[CH2:19][CH2:20]3)=[CH:11][C:10]=2[O:28][CH3:29])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 58071471HCID 58071471, compound2×

Product 1

HCID 58071454HCID 58071454, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

5-Bromo-N-(2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)-4-(1-tosyl-1H-indol-3-yl)pyrimidin-2-amine (INTERMEDIATE 37, 150 mg, 0.21 mmol) and Cs2CO3 (134 mg, 0.41 mmol) in 1:1 MeOH/THF (2.0 mL) was stirred at reflux for 2 h. The reaction mixture was filtered and concentrated in vacuo. The crude residue was purified by chromatography on silica gel (MeOH/1% NH4OH in DCM) to give the title product (131 mg, 69.5%).

Workup

  1. temperatureat reflux for 2 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by chromatography on silica gel (MeOH/1% NH4OH in DCM)

Sources & evidence

ORD record
ord-d2db9f34ac5c4b35a06949f8a346c853
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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