2-Bromo-3-methylpyridine → HCID 21101372, compound

HRID 2375477Notes

Reaction equation

HRID 2375477 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[N:12]=[C:11]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:10]=2)=[CH:4][CH:3]=1.Br[C:28]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[N:12]=[C:11]([N:21]3[CH2:22][CH2:23][N:24]([C:28]4[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:25][CH2:26]3)[N:10]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 2208322-Bromo-3-methylpyridineHCID 21101365HCID 21101365, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 21101372HCID 21101372, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-(4-methylphenyl)-2-(1-piperazinyl)-6-(1-piperidinyl)-4-pyrimidinamine (100 mg, 0.284 mmol), 2-bromo-3-methylpyridine (54 mg, 0.312 mmol), 1,1′-(bisdiphenylphosphino)-1,1′-binaphthol (13 mg), tris(dibenzylidene acetone)dipalladium(0) (13 mg), and sodium tert-butoxide (136 mg) in dry toluene (4 mL) was heated at 90° C. in a sealed tube for 2 hours. The reaction was quenched with water and the solution was extracted three times with ethyl acetate. The solvent was dried and removed. The crude material was purified by preparative. TLC, eluting with hexane/ethyl acetate (2:1). N-(4-methylphenyl)-2-[4-(3-methyl-2-pyridinyl)-1-piperazinyl]-6-(1-piperidinyl)-4-pyrimidinamine was obtained, from the band at Rf=0.46, as a solid (17.1 mg, 0.0385 mmol, 14%).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe solution was extracted three times with ethyl acetate
  3. customThe solvent was dried
  4. customremoved
  5. customThe crude material was purified by preparative
  6. washTLC, eluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-b693064e38c040fbb8a9b73dc139b18e
Source dataset
uspto-grants-2008_12
Patent number
US07465750B2

Reaction notes

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