Cesium carbonate → HCID 57897833, compound

HRID 1693575Notes

Reaction equation

HRID 1693575 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[N:14]=[CH:13][N:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27](B3OC(C)(C)C(C)(C)O3)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.[NH2:39][C:40]1[CH:45]=[CH:44][C:43](Br)=[CH:42][N:41]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:39][C:40]1[N:41]=[CH:42][C:43]([C:27]2[CH:28]=[CH:29][C:24]([C:9]3[N:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[C:16](=[O:17])[C:15]4[N:14]=[CH:13][N:12]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[C:11]=4[N:10]=3)=[CH:25][CH:26]=2)=[CH:44][CH:45]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 706222-Amino-5-bromopyridineHCID 57898052HCID 57898052, compound

Product 1

HCID 57897833HCID 57897833, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-(4-chloro-phenyl)-9-phenyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,9-dihydro-purin-6-one (180 mg, 0.34 mmol) and 2-amino-5-bromopyridine (89 mg, 0.51 mmol) in anhydrous DMF (3 mL) was treated sequentially with Cs2CO3 (224 mg, 0.69 mmol) and Pd(dppf)2Cl2 (14 mg, 0.017 mmol). The reaction mixture was degassed with N2 and heated at 100° C. for 24 h. The reaction was cooled to room temperature, diluted with H2O, and extracted with EtOAc. The combined organics were dried (MgSO4), filtered, and concentrated. The crude material was purified by flash column chromatography (silica, 30% EtOAc/CH2Cl2) to provide the title compound 2-[4-(6-amino-pyridin-3-yl)-phenyl]-1-(4-chloro-phenyl)-9-phenyl-1,9-dihydro-purin-6-one as a white solid. 1H NMR (CDCl3) δ (ppm) 8.19 (s, 1H), 7.95 (m, 2H), 7.72 (d, 2H), 7.61 (apparent t, 2H), 7.52 (apparent t, 1H), 7.42 (d, 2H), 7.35 (m, 4H), 7.17 (d, 2H), 6.95 (d, 1H); HPLC-MS calculated for C28H19ClN6O (M+H+): 491.1. Found: 491.1.

Workup

  1. customThe reaction mixture was degassed with N2
  2. temperatureThe reaction was cooled to room temperature
  3. additiondiluted with H2O
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by flash column chromatography (silica, 30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-a377abf4f2c94c1e9924791882d85818
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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