Cesium carbonate → HCID 58318856, compound

HRID 2401503Notes

Reaction equation

HRID 2401503 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].[NH2:11][C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>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(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.O1CCOCC1>[F:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)[CH:9]=1)[C:5]#[N:6]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 344373Pyrimidin-5-amineHCID 27833303-Bromo-5-fluorobenzonitrile

Product 1

HCID 58318856HCID 58318856, compoundYield 121.4%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

3-Bromo-5-fluorobenzonitrile (1.0 g, 5.0 mmol, 1.0 eq), 5-aminopyrimidine (571 mg, 6.00 mmol, 1.20 eq), Cs2CO3 (2.28 g, 7.00 mmol, 1.40 eq), Pd2(dba)3 (230 mg, 0.400 mmol, 0.0800 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (347 mg, 0.600 mmol, 0.120 eq) and dioxane (12.5 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 1.3 g (65%) of the title compound as an orange solid: 1H NMR (400 MHz, CDCl3) δ 9.06 (s, 1H), 8.80 (s, 2H), 8.67 (s, 1H), 7.32-7.30 (m, 1H), 7.28-7.24 (m, 1H), 7.21 (dt, J=11.3, 2.2 Hz, 1H); [M+1]+: 215.2.

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-0b76addd273e41d5adbd9f29ebd9356c
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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