Cesium carbonate → 6-[3-(2-Fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-1,3,5-triazine-2,4-diamine

HRID 1875451Notes

Reaction equation

HRID 1875451 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[NH:7][N:6]=1.Cl[C:19]1[N:24]=[C:23]([NH2:25])[N:22]=[C:21]([NH2:26])[N:20]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.CO>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N:7]([C:19]2[N:24]=[C:23]([NH2:25])[N:22]=[C:21]([NH2:26])[N:20]=2)[N:6]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 188311,3,5-Triazine-2,4-diamine, 6-chloro-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178505620HCID 178505620, compound

Product 1

HCID 247944786-[3-(2-Fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-1,3,5-triazine-2,4-diamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 100 mg (0.44 mmol) of 3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridine from example 4A, 64 mg (0.44 mmol) of 6-chloro-1,3,5-triazine-2,4-diamine, 8.1 mg (0.009 mmol) of tris(di-benzylideneacetone)dipalladium, 13 mg (0.026 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPHOS) and 201 mg (0.62 mmol) of cesium carbonate in 3 ml of degassed toluene is heated at 90° C. for 20 h. It is then diluted with ethyl acetate and methanol, filtered and concentrated in vacuo. The residue is crystallized from methanol to result in 42 mg (28% of theory) of the title compound as pale yellow crystals.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-7798a090ab7e47c79d83f8968a76ff38
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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