Cesium carbonate → HCID 58349171, compound

HRID 1045817Notes

Reaction equation

HRID 1045817 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[NH2:9][C:10]1[CH:11]=[N:12][CH:13]=[N:14][CH:15]=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:8][C:6]1[CH:7]=[C:2]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)[CH:3]=[N:4][CH:5]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 693693,5-DibromopyridineHCID 344373Pyrimidin-5-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 58349171HCID 58349171, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

3,5-Dibromopyridine (0.30 g, 1.3 mmol, 1.0 eq), 5-aminopyrimidine (120 mg, 1.26 mmol, 1.00 eq), Cs2CO3 (578 mg, 1.77 mmol, 1.40 eq), Pd2(dba)3 (58 mg, 0.10 mmol, 0.080 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (88 mg, 0.15 mmol, 0.12 eq) and toluene (4.2 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 175 mg (55%) of the title compound as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 8.95 (bs, 1H), 8.76 (s, 1H), 8.64 (s, 2H), 8.37 (d, J=2.4 Hz, 1H), 8.20 (d, J=2.0 Hz, 1H), 7.73 (t, J=2.2 Hz, 1H); [M+1]+: 251.1.

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-b7403ce3e5c94722a22c8ca94515cea2
Source dataset
uspto-grants-2013_10
Patent number
US08569308B2

Reaction notes

Loading…