Sodium Carbonate → HCID 57825100, compound

HRID 1668769Notes

Reaction equation

HRID 1668769 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:12]([CH3:13])[O:11][C:10]([NH2:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[N:23]1[CH:28]=[C:27](B(O)O)[CH:26]=[N:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:27]4[CH:28]=[N:23][CH:24]=[N:25][CH:26]=4)[CH:3]=3)[CH:12]([CH3:13])[O:11][C:10]([NH2:14])=[N:9]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 57825249HCID 57825249, compound

Product 1

HCID 57825100HCID 57825100, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A dried pressure tube was charged with (4RS,5RS)-4-(3-bromo-phenyl)-4-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazol-2-ylamine (Building Block AP, (64 mg, 0.2 mmol), pyrimidine-5-boronic acid (25 mg, 0.2 mmol), triphenylphosphine (10 mg, 0.04 mmol), 2 N sodium carbonate solution (0.4 mL), and 1,2-dimethoxyethane (2 mL). The mixture was purged with argon before palladium(II)acetate (4 mg, 0.018 mmol) was added. The sealed pressure tube was heated at 100° C. for 60 hours. The incomplete reaction was stopped, the reaction mixture was cooled and evaporated under reduced pressure. The residue was directly chromatographed on silica gel using a gradient of dichloromethane/methanol=100/0 to 85/15 as the eluent. The mixture of the diastereomeric racemates was chromatographed on a preparative silica gel LC-plate using a 9:1-mixture of dichloromethane/methanol as the eluent. There were obtained 2 fractions of the desired product: 5 mg of a 9:1-mixture of diastereomeric racemates (example 169) [Mass (calculated) C21H20N4O2 [360]; (found) [M+H]+=361 and 3 mg of a 6:4-mixture of diastereomeric racemates (example 170) [Mass (calculated) C21H20N4O2 [360]; (found) [M+H]+=361

Workup

  1. additionwas added
  2. customThe incomplete reaction
  3. temperaturethe reaction mixture was cooled
  4. customevaporated under reduced pressure
  5. customThe residue was directly chromatographed on silica gel using a gradient of dichloromethane/methanol=100/0 to 85/15 as the eluent
  6. additionThe mixture of the diastereomeric racemates
  7. customwas chromatographed on a preparative silica gel LC-plate

Sources & evidence

ORD record
ord-4ed5760195ae4d1ba005e13b441f8676
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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