Cesium carbonate → HCID 58337464, compound

HRID 1887459Notes

Reaction equation

HRID 1887459 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4]([Br:9])[CH:3]=1.[NH2:10][C:11]1[CH:12]=[N:13][CH:14]=[N:15][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Br:9][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 846761,3-Dibromo-5-chlorobenzeneHCID 344373Pyrimidin-5-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 58337464HCID 58337464, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1-chloro-3,5-dibromobenzene (0.30 g, 1.1 mmol, 1.0 eq), 5-aminopyrimidine (106 mg, 1.11 mmol, 1.00 eq), Cs2CO3 (506 mg, 1.55 mmol, 1.40 eq), Pd2(dba)3 (51 mg, 0.089 mmol, 0.080 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (77 mg, 0.13 mmol, 0.12 eq) and toluene (3.7 mL) were added to a microwave vial. The vial was purged with argon, capped and heated at 100° C. for 18 h. After cooling the reaction was filtered over a plug of celite and the plug was washed with 5% MeOH/CH2Cl2. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 173 mg (55%) of the title compound as a light-orange solid: 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.77 (s, 1H), 8.62 (s, 2H), 7.18 (t, J=1.8 Hz, 1H), 7.15 (t, J=1.7 Hz, 1H), 7.09 (t, J=1.9 Hz, 1H); ES-MS [M+1]+: 284.0.

Workup

  1. customThe vial was purged with argon
  2. customcapped
  3. temperatureAfter cooling the reaction
  4. filtrationwas filtered over a plug of celite
  5. washthe plug was washed with 5% MeOH/CH2Cl2
  6. customThe solvents were removed in vacuo
  7. customthe crude mixture was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-6adbdc09a9cf43f481f8da3ed648fed1
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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