Cesium carbonate → HCID 57675075, compound

HRID 1095053Notes

Reaction equation

HRID 1095053 reaction equation
[CH3:1][C:2]1[C:3]([NH2:23])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:24][C:25]1([CH3:65])[C:51]2[C:46](=[C:47](P(C3C=CC=CC=3)C3C=CC=CC=3)[CH:48]=[CH:49][CH:50]=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:26]1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:18]1([CH2:17][CH2:16][O:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:5]3[N:4]=[C:3]([NH:23][C:5]4[N:4]=[C:3]([NH:23][C:47]5[CH:48]=[CH:49][CH:50]=[C:51]([C:25]([CH3:24])([CH3:26])[CH3:65])[CH:46]=5)[C:2]([CH3:1])=[CH:7][N:6]=4)[C:2]([CH3:1])=[CH:7][N:6]=3)=[CH:14][CH:13]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 576750855-Methyl-N2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine

Product 1

HCID 57675075HCID 57675075, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of intermediate 41 (210 mg, 0.67 mmol), intermediate 38 (185 mg, 0.67 mmol), Pd2(dba)3 (55 mg, 0.06 mmol). Xantphos (104 mg, 0.18 mmol) and cesium carbonate (782 g, 2.4 mmol) were suspended in dioxane (50 mL) and heated at reflux under the argon atmosphere for 20 h. The mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by HPLC to afford the title compound (94 mg of HCl salt, 24%) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux under the argon atmosphere for 20 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-42f663995d2d425aa6cf3157632833b0
Source dataset
uspto-grants-2012_03
Patent number
US08133900B2

Reaction notes

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