Triethylamine → 4-(1H-5-indolyloxy)-2-pyrimidinamine

HRID 2264600Notes

Reaction equation

HRID 2264600 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:5]=[C:4](Cl)[N:3]=1.CCN(CC)CC>C1COCC1.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 219493934-Chloro-6-(1H-5-indolyloxy)-2-pyrimidinamine

Product 1

HCID 219492624-(1H-5-indolyloxy)-2-pyrimidinamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.00 g (3.84 mMol) 5-(2-amino-6-chloro-pyrimidin-4-yloxy)-1H-indole (Step 24.1) and 562 μl (4.0 mMol) Et3N in 170 ml THF is hydrogenated in the presence of 0.7 g Pd/C (10%; Engelhard 4505). The catalyst is filtered off, the filtrate concentrated and the residue dissolved in EtOAc and H2O. The aqueous layer is extracted twice with water. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; EtOAc/hexane 4:1) gives the title compound: MS: [M+1]+=227; TLC(EtOAc/hexane 4:1): Rf=0.4; HPLC: AtRet=8.5.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate concentrated
  3. dissolutionthe residue dissolved in EtOAc
  4. extractionThe aqueous layer is extracted twice with water
  5. washThe organic layers are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7af756c055e64452a9c8e3a61535833f
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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