Cesium carbonate → HCID 24794432, compound

HRID 1875454Notes

Reaction equation

HRID 1875454 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][N:12]=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>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][N:12]=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

7

Reactant 4

HCID 10796Cesium carbonateHCID 188311,3,5-Triazine-2,4-diamine, 6-chloro-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178505622HCID 178505622, compound

Product 1

HCID 24794432HCID 24794432, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 144 mg (0.63 mmol) of 3-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyrazine from example 14A, 92 mg (0.63 mmol) of 6-chloro-1,3,5-triazine-2,4-diamine, 12 mg (0.013 mmol) of tris(di-benzylideneacetone)dipalladium, 18 mg (0.038 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPHOS) and 287 mg (0.88 mmol) of cesium carbonate in 4 ml of degassed toluene is heated at 90° C. for 20 h. It is then diluted with ethyl acetate and a little methanol and filtered with suction. The solid is again stirred with methanol and filtered off with suction once again. The filtrates are then combined and concentrated, and the residue is purified by preparative HPLC. The product fraction obtained is concentrated, again stirred with methanol and filtered off with suction. 13 mg (6% of theory) of the desired product are obtained in this way.

Workup

  1. filtrationa little methanol and filtered with suction
  2. filtrationfiltered off with suction once again
  3. concentrationconcentrated
  4. customthe residue is purified by preparative HPLC
  5. customThe product fraction obtained
  6. concentrationis concentrated
  7. stirringagain stirred with methanol
  8. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-c1ace4dc313a4425b21b49db1e301ba4
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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