Sodium Carbonate → HCID 90017824, compound

HRID 1486533Notes

Reaction equation

HRID 1486533 reaction equation
[CH:1]([N:14]1[CH:19]=[C:18](I)[C:17](=[O:21])[NH:16][C:15]1=[O:22])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(C)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:1]([N:14]1[CH:19]=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17](=[O:21])[NH:16][C:15]1=[O:22])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 21863594Toluene ethanolHCID 716549651-Benzhydryl-5-iodo-pyrimidine-2,4-dione

Product 1

HCID 90017824HCID 90017824, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1-Benzhydryl-5-iodo-pyrimidine-2,4-dione (0.06 g, 0.15 mmol) was suspended in a 1:1 toluene/ethanol mixture (1,6 Phenylboronic acid (0.03 g, 0.22 mmol) was added followed by 2M aqueous solution of sodium carbonate (0.082 mL, 0.16 mmol). The resulting suspension was degassed under nitrogen atmosphere for 10 min, then tetrakis(triphenylphosphine) palladium(0) (0.017 g, 0.015 mmol) was added. The reaction was heated under microwave irradiation at 100° C. for 30 min. The reaction mixture was diluted with EtOAc and water was added. The two phases were separated and the aqueous layer was extracted with EtOAc (3×15 mL). The combined organic phases were dried over Na2SO4 and the solvent was removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 60:40) to afford the title compound (0.03 g, 62%) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.13 (s, 1H), 7.20-7.24 (m, 5H), 7.25 (s, 1H), 7.32-7.35 (m, 5H), 7.37-7.44 (m, 5H), 8.19 (br s, 1H). MS (ESI) to/z: 355 [M-H]+.

Workup

  1. additionwas added
  2. customThe resulting suspension was degassed under nitrogen atmosphere for 10 min
  3. additionwas added
  4. customThe two phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×15 mL)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. customthe solvent was removed under reduced pressure
  8. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-20a472e1d2654df69a3beb3f6f2a7269
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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