1,2-Dimethoxyethane → HCID 24745735, compound

HRID 1418076Notes

Reaction equation

HRID 1418076 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.[OH-].[Ba+2].[OH-].COCCOC>O>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:5]1[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 2313102-Amino-5-bromopyrimidineHCID 2762745Pyridine-2-boronic acidHCID 6093286Barium hydroxide

Product 1

HCID 24745735HCID 24745735, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-amino-5-bromopyrimidine (0.299 g, 1.72 mmol), 2-pyridylboronic acid (1.57 g, 12.79 mmol), barium hydroxide (0.813 mg, 2.58 mmol), DME (8 mL) and water (1.5 mL) is purged with dry argon. Tetrakis(triphenylphosphine) palladium(0) (99.0 mg, 0.086 inmol) is added, and the resultant solution is stirred at 80° C. for 4 hours. The solvents are evaporated in vacuo, and the residue is partitioned between EtOAc and water. The aqueous extract is separated, and extracted with EtOAc. The organic extracts are combined, washed with sat. aq. NaHCO3 and 5% aq. Na2S2O3, dried, (Na2SO4) and the solvent is evaporated in vacuo. The residue is purified by chromatography to afford the title compound.

Workup

  1. customis purged with dry argon
  2. additionTetrakis(triphenylphosphine) palladium(0) (99.0 mg, 0.086 inmol) is added
  3. customThe solvents are evaporated in vacuo
  4. customthe residue is partitioned between EtOAc and water
  5. extractionThe aqueous extract
  6. customis separated
  7. extractionextracted with EtOAc
  8. washwashed with sat. aq. NaHCO3 and 5% aq. Na2S2O3
  9. customdried
  10. custom(Na2SO4) and the solvent is evaporated in vacuo
  11. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-598610fa774b49cf9cb3df4698ff8225
Source dataset
uspto-grants-1999_03
Patent number
US05880140

Reaction notes

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