Ethanol → HCID 15838742, compound

HRID 343845Notes

Reaction equation

HRID 343845 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:14][C:15]1[N:20]=[C:19](Cl)[C:18]([CH3:22])=[C:17]([CH3:23])[N:16]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC.O>[NH2:14][C:15]1[N:20]=[C:19]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:18]([CH3:22])=[C:17]([CH3:23])[N:16]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2486554-chloro-5,6-dimethylpyrimidin-2-amineHCID 2545321-Naphthaleneboronic acid

Product 1

HCID 15838742HCID 15838742, compoundYield 38.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred heterogeneous solution of 1-naphthyl boronic acid (0.382 g), 2-amino-4-chloro-5,6-dimethylpyrimidine (0.350 g), tetrakis(triphenylphosphine)palladium(0) (0.153 g), ethyl alcohol (8 mL), water (4 mL), 1,2-dimethoxyethane (8 mL) and sodium carbonate (0.85 g), was heated to reflux (about 80° to 90° C.) for 14 hours. The solution was then cooled to room temperature, filtered and extracted with ethyl acetate. The solvent was removed under reduced pressure and the resultant yellow solid was recrystallized to give 2-amino-5,6-dimethyl-4-(naphth-1-yl)-pyrimidine (0.213 g), m.p. 213.5°-215.1° C.

Workup

  1. temperatureto reflux (about 80° to 90° C.) for 14 hours
  2. filtrationfiltered
  3. extractionextracted with ethyl acetate
  4. customThe solvent was removed under reduced pressure
  5. customthe resultant yellow solid was recrystallized

Sources & evidence

ORD record
ord-4aedc9dcbb67490d88439b413074bb28
Source dataset
uspto-grants-1999_01
Patent number
US05863924

Reaction notes

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