{4-[2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-6-methyl-pyrimidin-2-yl}-isopropyl-amine → 2-Ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenol

HRID 2069473Notes

Reaction equation

HRID 2069473 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH:28][CH:29]([CH3:31])[CH3:30])[N:22]=3)=[CH:19][N:20]=2)=[CH:11][C:10]=1[CH2:32][CH3:33])C1C=CC=CC=1>C1COCC1.CO.[Pd]>[CH2:32]([C:10]1[CH:11]=[C:12]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH:28][CH:29]([CH3:30])[CH3:31])[N:22]=3)=[CH:19][N:20]=2)[CH:13]=[C:14]([CH3:15])[C:9]=1[OH:8])[CH3:33]

Participants

5

Reactant 1

HCID 68505777{4-[2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-6-methyl-pyrimidin-2-yl}-isopropyl-amine

Product 1

HCID 1363463712-Ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenolYield 97.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 23938PalladiumSolvent

Procedure

To a solution of {4-[2-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-6-methyl-pyrimidin-2-yl}-isopropyl-amine (27 mg, 61 μmol) in THF (2 mL) and MeOH (2 mL), 10% Pd/C is added (50 mg). The reaction mixture is stirred under H2 atmosphere for 18 h, and is filtered through celite. The filtrate is evaporated to give 2-ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenol (21 mg) as a yellow oil; LC-MS: tR=0.88 min, [M+H]+=353.03.

Workup

  1. filtrationis filtered through celite
  2. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-814e4a0f3f9c4c37a80ecb6160361f52
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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