Cesium carbonate → HCID 69281440, compound

HRID 2409097Notes

Reaction equation

HRID 2409097 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=1.[CH:14]([N:17]1[CH:21]=[C:20]([NH2:22])[CH:19]=[N:18]1)([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>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].O1CCOCC1>[CH:14]([N:17]1[CH:21]=[C:20]([NH:22][C:2]2[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=2)[CH:19]=[N:18]1)([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 134698261-(Propan-2-yl)-1H-pyrazol-4-amineHCID 210775872-Chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine

Product 1

HCID 69281440HCID 69281440, compoundYield 16.7%

Reagents, catalysts & solvents 2

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

Procedure

To a microwave tube was added 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (112 mg, 0.53 mmol), 1-isopropyl-1H-pyrazol-4-amine (55 mg, 0.44 mmol), cesium carbonate (0.287 g, 0.88 mmol), XPhos (21 mg, 0.044 mmol), Pd2(dba)3 (20 mg, 0.02 mmol) and dioxane (2.5 mL). The tube was sealed and the reaction was irradiated in the microwave at 140° C. for 30 minutes. The reaction mixture was then filtered and concentrated. The crude product was purified by reverse phase HPLC to give N2-(1-isopropyl-1H-pyrazol-4-yl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine (22 mg, 16%). LCMS (Method A): [MH+]=301.1 at 3.2 min. 1H-NMR (DMSO): δ 9.43 (m, 2H), 8.08 (s, 1H), 7.89 (s, 1H), 7.54 (s, 1H), 6.96 (m, 2H), 4.43 (m, 1H), 2.92 (d, J=8.0, 3H), 1.39 (d, J=6.6, 6H).

Workup

  1. customThe tube was sealed
  2. customthe reaction was irradiated in the microwave at 140° C. for 30 minutes
  3. filtrationThe reaction mixture was then filtered
  4. concentrationconcentrated
  5. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2bddf326129241e5a37ab2b704a91cb7
Source dataset
uspto-grants-2014_08
Patent number
US08815882B2

Reaction notes

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