1-{4-[4-(3,6-dihydro-2H-pyran-4-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-phenyl}-3-pyridin-4-yl-urea → 1-{4-[4-Morpholin-4-yl-6-(tetrahydro-pyran-4-yl)-[1,3,5]triazin-2-yl]-phenyl}-3-pyridin-4-yl-urea

HRID 536844Notes

Reaction equation

HRID 536844 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)=[O:27])=[CH:21][CH:20]=3)[N:8]=2)[CH2:3][CH2:2]1>CO.C1COCC1.C(Cl)Cl.[Pd]>[N:13]1([C:11]2[N:12]=[C:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[N:8]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]4[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=4)=[O:27])=[CH:21][CH:20]=3)[N:10]=2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

4

Reactant 1

HCID 445125731-{4-[4-(3,6-dihydro-2H-pyran-4-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-phenyl}-3-pyridin-4-yl-urea

Product 1

HCID 445125741-{4-[4-Morpholin-4-yl-6-(tetrahydro-pyran-4-yl)-[1,3,5]triazin-2-yl]-phenyl}-3-pyridin-4-yl-ureaYield 24.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22912779methanol THF dichloromethaneSolvent

Procedure

1-{4-[4-(3,6-dihydro-2H-pyran-4-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-phenyl}-3-pyridin-4-yl-urea (130 mg, 0.28 mmol) and Pd—C (10%, wet) (113 mg) were suspended in methanol/THF/CH2Cl2 (4:1:1) (30 mL) and hydrogenated (at 1 atm pressure) for 3 h. After completion, the catalyst was removed by filtration over Celite™ and the solvents were removed in vacuo to obtain the crude product, which was purified by semi-prep-HPLC (TFA-method), to give (32 mg=20% yield) of 1-{4-[4-Morpholin-4-yl-6-(tetrahydro-pyran-4-yl)-[1,3,5]triazin-2-yl]-phenyl}-3-pyridin-4-yl-urea; MS (ESI) m/z 462.

Workup

  1. customAfter completion, the catalyst was removed by filtration over Celite™
  2. customthe solvents were removed in vacuo
  3. customto obtain the crude product, which
  4. customwas purified by semi-prep-HPLC (TFA-method)

Sources & evidence

ORD record
ord-aa80fe21313042fe9c1c0cda2a50f59e
Source dataset
uspto-grants-2014_10
Patent number
US08859542B2

Reaction notes

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