Sodium Hydroxide → HCID 86645307, compound

HRID 2069427Notes

Reaction equation

HRID 2069427 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:2].[OH-].[Na+].[CH2:30]1[O:32][C@H:31]1[CH2:33]Cl>C(O)(C)C.CCOC(C)=O>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:33][C@@H:31]4[CH2:30][O:32]4)=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:27]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2734062(-)-EpichlorohydrinHCID 136339878HCID 136339878, compound

Product 1

HCID 86645307HCID 86645307, compoundYield 109.6%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[5-(2-diethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol (700 mg, 1.90 mmol) in isopropanol (12 mL), are added 3M aq. NaOH (4 mL) and R-epichlorohydrine (1.49 mL, 19.0 mmol). The reaction mixture is stirred at rt for 15 h, then is diluted with EtOAc and washed with 1M aq. NaOH followed by brine. The org. phase is dried over Na2SO4, filtered, evaporated and purified by CC (eluting with Heptane/EtOAc 4:1) to give the title compound as a yellow oil (882 mg); LC-MS: tR=1.23; [M+H]+=424.04. 1H NMR (CDCl3) δ 1.25 (t, J=7.0 Hz, 6H), 1.33 (t, J=7.5 Hz, 3H), 2.41 (s, 3H), 2.47 (s, 3H), 2.79 (m, 3H), 2.94 (t, J=4.5 Hz, 1H), 3.42 (m, 1H), 3.76 (q, J=7.0 Hz, 4H), 3.83 (dd, J=11.0, 5.8 Hz, 1H), 4.13 (dd, J=11.0, 3.0 Hz, 1H), 7.23 (s, 1H), 7.89 (d, J=5.5 Hz, 2H).

Workup

  1. washwashed with 1M aq. NaOH
  2. dry with materialphase is dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by CC (eluting with Heptane/EtOAc 4:1)

Sources & evidence

ORD record
ord-a737585777d74859add0215c0cb61f63
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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