Potassium Phosphate, Tribasic → HCID 53257453, compound

HRID 576675Notes

Reaction equation

HRID 576675 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[CH:3]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[CH:3]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27339582-Methoxyphenylboronic acidHCID 53257454HCID 53257454, compound

Product 1

HCID 53257453HCID 53257453, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.739 g 2-[3-(6-Chloro-pyrimidin-4-ylamino)-benzyl]-isoindole-1,3-dione (prepared in Example 67) (4.79 mmol) was suspended in 50 cm3 abs. DMF and the flask was filled with argon properly. 347 mg Tetrakis(thriphenylphosphine) palladium[0] (0.3 mmol) was added and the mixture was stirred at room temperature for 30 minutes. Then 968 mg 2-methoxyphenyl-boronic acid (6.50 mmol) and 2.123 g K3PO4 (3 mmol) was added. The mixture was ferluxed for 6 hours while slow argon flow was being applied. The reaction mixture was evaporated under reduced pressure, 150 cm3 5% NaHCO3 solution was added and it was extracted three times with 100-100 cm3 of ethyl-acetate. The combined organic layer was washed with brine, dried over MgSO4, decolorized with activated carbon and evaporated under reduced pressure. The residual oil was chromatographed on silica gel eluting with chloroform containing 1% ethyl-alcohol. The residual solid was recrystallized from minimal amount of acetonitrile and air-dried to give the desired product as a yellow solid. Yield: 1.652 g (79%). For analitical results and compound identification see Table 1.

Workup

  1. waitThe mixture was ferluxed for 6 hours while slow argon flow
  2. customThe reaction mixture was evaporated under reduced pressure, 150 cm3 5% NaHCO3 solution
  3. additionwas added
  4. extractionit was extracted three times with 100-100 cm3 of ethyl-acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure
  8. customThe residual oil was chromatographed on silica gel eluting with chloroform containing 1% ethyl-alcohol
  9. customThe residual solid was recrystallized from minimal amount of acetonitrile
  10. customair-dried

Sources & evidence

ORD record
ord-5cdd0f1875b64988bf55a088abb9b28b
Source dataset
uspto-grants-2015_05
Patent number
US09040529B2

Reaction notes

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