Trifluoroacetic acid → [2-(5-Chloro-2-fluoro-phenyl)-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl]-(3-methyl-pyridin-4-yl)-amine

HRID 1354309Notes

Reaction equation

HRID 1354309 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C:8]2[N:13]=[C:12](I)[C:11]3[CH2:15][C:16]([CH3:19])([CH3:18])[CH2:17][C:10]=3[N:9]=2)[CH:7]=1.[CH3:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[NH2:28].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].C(O)(C(F)(F)F)=O>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C:8]2[N:13]=[C:12]([NH:28][C:27]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=3[CH3:21])[C:11]3[CH2:15][C:16]([CH3:19])([CH3:18])[CH2:17][C:10]=3[N:9]=2)[CH:7]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 748113-Methyl-4-pyridinamineHCID 634876Binap, (A+-)-HCID 211043092-(5-Chloro-2-fluoro-phenyl)-4-iodo-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidine

Product 1

HCID 21104318[2-(5-Chloro-2-fluoro-phenyl)-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl]-(3-methyl-pyridin-4-yl)-amine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-(5-Chloro-2-fluoro-phenyl)-4-iodo-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidine (100 mg, 0.25 mmol), 3-Methyl-pyridin-4-ylamine (30 mg, 0.27 mmol), Pd(OAc)2 (3 mg, 12.42 μmol) and Rac-BINAP (12 mg, 18.63 μmol) in dry dioxane (3 mL) was added Cs2CO3 (121 mg, 0.37 mmol). The mixture was heated for 48 h at 85° C., cooled and evaporated. HPLC purification gave, after lyophilization, the desired product 60 as the TFA salt, a white solid (6.4 mg).

Workup

  1. temperaturecooled
  2. customevaporated
  3. customHPLC purification
  4. customgave

Sources & evidence

ORD record
ord-72f06c0b79754239898f3a1870957b4e
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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