Cesium carbonate → Methyl 4'-(2-(4-cyanophenylamino)-9-methyl-9H-purin-6-yloxy)-3',5'-dimethylbiphenyl-4-carboxylate

HRID 222079Notes

Reaction equation

HRID 222079 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=3)=[CH:15][C:14]=2[CH3:30])[N:3]=1.[NH2:31][C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:36]([C:35]1[CH:38]=[CH:39][C:32]([NH:31][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH3:11])=[C:4]([O:12][C:13]3[C:18]([CH3:19])=[CH:17][C:16]([C:20]4[CH:21]=[CH:22][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:25]=4)=[CH:15][C:14]=3[CH3:30])[N:3]=2)=[CH:33][CH:34]=1)#[N:37]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 133964-AminobenzonitrileHCID 634876Binap, (A+-)-HCID 57747321Methyl 4'-(2-chloro-9-methyl-9H-purin-6-yloxy)-3',5'-dimethylbiphenyl-4-carboxylate

Product 1

HCID 57747379Methyl 4'-(2-(4-cyanophenylamino)-9-methyl-9H-purin-6-yloxy)-3',5'-dimethylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A degassed solution of methyl 4′-(2-chloro-9-methyl-9H-purin-6-yloxy)-3′,5′-dimethylbiphenyl-4-carboxylate (180 mg, 0.43 mmol), 4-aminobenzonitrile (105 mg, 0.89 mmol), Pd(OAc)2 (10 mg, 0.044 mmol), BINAP (57 mg, 0.092 mmol), and Cs2CO3 (280 mg, 0.88 mmol) in toluene (2 mL) was heated at 80° C. overnight. The desired product was precipitated with EtOAc (2 mL) and saturated NaHCO3 (2 mL) and the resulting precipitate was collected by filtration (210 mg). NMR (DMSO-d6): δ 10.10 (s, 1H), 8.25 (s, 1H), 8.10 (d, 2H), 7.95 (d, 2H), 7.68 (s, 2H), 7.60 (d, 2H), 7.34 (d, 2H), 3.91 (s, 3H), 3.80 (s, 3H), 2.18 (s, 6H); MS (ESI): m/z 505 (M+1)+.

Workup

  1. customThe desired product was precipitated with EtOAc (2 mL) and saturated NaHCO3 (2 mL)
  2. filtrationthe resulting precipitate was collected by filtration (210 mg)

Sources & evidence

ORD record
ord-feae20fe93204c858fe2447a58404032
Source dataset
uspto-grants-2012_06
Patent number
US08207178B2

Reaction notes

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