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

HRID 1352893Notes

Reaction equation

HRID 1352893 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 TLC
  6. washeluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8e80780d9e9347928e9b79dbb44e85a2
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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