{3-[2-Chloro-5-(3,6-dihydro-2H-pyran-4-YL)-pyrimidin-4-yloxy]-cyclobutyl}-carbamic acid tert-butyl ester → {3-[5-(Tetrahydro-pyran-4-YL)-pyrimidin-4-yloxy]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1846826Notes

Reaction equation

HRID 1846826 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:11][CH:10]([O:12][C:13]2[C:18]([C:19]3[CH2:20][CH2:21][O:22][CH2:23][CH:24]=3)=[CH:17][N:16]=[C:15](Cl)[N:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:9][CH:10]([O:12][C:13]2[C:18]([CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:17][N:16]=[CH:15][N:14]=2)[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58548678{3-[2-Chloro-5-(3,6-dihydro-2H-pyran-4-YL)-pyrimidin-4-yloxy]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 58548573{3-[5-(Tetrahydro-pyran-4-YL)-pyrimidin-4-yloxy]-cyclobutyl}-carbamic acid tert-butyl esterYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of {3-[2-chloro-5-(3,6-dihydro-2H-pyran-4-yl)-pyrimidin-4-yloxy]-cyclobutyl}-carbamic acid tert-butyl ester (2.2 g, 5.76 mmol) in MeOH (40 mL) was added Pd/C (1.0 g). The reaction solution was stirred at room temperature overnight under H2 atmosphere. LCMS showed that the staring material was consumed completely. The mixture was filtered and concentrated to give the product (1.2 g, 3.44 mmol, yield: 60%). ESI-MS (M+1): 350 calc. for C18H27N3O4 349.

Workup

  1. customwas consumed completely
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fc43c157efdd454f9930d80a2d072255
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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