Sodium Carbonate → 1-(4-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol

HRID 1161672Notes

Reaction equation

HRID 1161672 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)[N:3]=1.[C:21](=[O:24])([O-])[O-:22].[Na+].[Na+]>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:22]1[C:9]2[CH:10]=[CH:11][C:12]([C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:5]=[C:4]([N:14]4[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]4)[N:3]=3)=[CH:13][C:8]=2[O:24][CH2:21]1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 586261271-(4-Chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol

Product 1

HCID 114945441-(4-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of compound benzo[1,3]dioxo-5-yl boronic acid (0.14 g, 83 mmol), and compound 1-(4-chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol (90.2 g, 69 mmol), (PPh3)4Pd (31 mg, 0.03 mmol) and sodium carbonate (0.73 g, 69 mmol) in dimethylformamide (5 mL) was stirred for 1 hour at 25° C. and then for 12 hours at 80° C. under nitrogen atmosphere. The mixture was cooled to temperature in the range of 20-40° C., diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The organic layers were collected, combined, washed with water (10 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum. The residue thus obtained was purified by column chromatography using ethyl acetate-petroleum ether to give the desired compound.

Workup

  1. waitfor 12 hours at 80° C. under nitrogen atmosphere
  2. temperatureThe mixture was cooled to temperature in the range of 20-40° C.
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. customThe organic layers were collected
  5. washwashed with water (10 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under vacuum
  8. customThe residue thus obtained
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6203cb15243e4698badfaf7fb1e7692b
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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