Triethylamine → HCID 59837411, compound

HRID 272987Notes

Reaction equation

HRID 272987 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][C:10]2([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:18][CH:17]=3)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:3]=1.C(N(CC)CC)C>C(O)C.[Pd]>[N:26]1([CH2:25][CH2:24][CH2:23][O:22][C:19]2[CH:18]=[CH:17][C:16]([C:10]3([CH2:9][NH:8][C:4]4[CH:3]=[CH:2][N:7]=[CH:6][N:5]=4)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[CH:21][CH:20]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86601905HCID 86601905, compound

Product 1

HCID 59837411HCID 59837411, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-chloro-N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)pyrimidin-4-amine (50 mg, 0.12 mmol) and triethylamine (48.6 μl, 0.35 mmol) in ethanol (2 mL) was hydrogenated for 16 hours at room temperature at 50 psi in the presence of 10% Pd/C (5 mg, 10% w/w). The reaction mixture was filtered through Arbocel® and rinsed with ethanol and water. The filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate (20 ml) and saturated aqueous sodium carbonate (20 ml). The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 95:5:0.5 by volume) to provide the title compound (9 mg, 20%).

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel®
  2. washrinsed with ethanol and water
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate (20 ml) and saturated aqueous sodium carbonate (20 ml)
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 95:5:0.5 by volume)

Sources & evidence

ORD record
ord-cf7f94aeb7804e0ebd108ccf3fab9b79
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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