Triethylamine → HCID 58863898, compound

HRID 1352902Notes

Reaction equation

HRID 1352902 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:6]=[C:5]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:4]=1.Cl[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:33][O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][N:20]1[CH2:19][CH2:18][N:17]([C:5]2[N:4]=[C:3]([N:2]([CH3:1])[CH3:23])[CH:8]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=3)[N:6]=2)[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 814952-(Chloromethyl)anisoleHCID 516892Sodium BicarbonateHCID 86587737HCID 86587737, compound

Product 1

HCID 58863898HCID 58863898, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of N4,N4-dimethyl-N6-(4-methylphenyl)-2-(1-piperazinyl)-4,6-pyrimidinediamine (30 mg, 0.086 mmol), 1-(chloromethyl)-2-methoxybenzene (17 mg, 0.1 mmol) and triethylamine (200 mg, 2 mmol) in 1 DMF (1 mL) heated by microwave at 200° C. for 12 minutes. The crude product was treated with saturated NaHCO3 (50 mL) and extracted with EtOAC (3×50 mL). The organic layer was washed with brine (2×100 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica using hexane/EtOAc (1:3), giving the desired product (10 mg, 27%).

Workup

  1. extractionextracted with EtOAC (3×50 mL)
  2. washThe organic layer was washed with brine (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography on silica

Sources & evidence

ORD record
ord-2f3dcd9a64764c2e85b0b3fc0584d138
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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