Diisopropylethylamine → (S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one

HRID 1850212Notes

Reaction equation

HRID 1850212 reaction equation
Cl.[NH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)[CH3:4].F[C:14]1[N:19]=[C:18]([N:20]2[C@@H:24]([CH:25]([CH3:27])[CH3:26])[CH2:23][O:22][C:21]2=[O:28])[CH:17]=[CH:16][N:15]=1.CCN(C(C)C)C(C)C>CS(C)=O.CCOC(C)=O>[OH:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C@@H:3]([NH:2][C:14]2[N:19]=[C:18]([N:20]3[C@@H:24]([CH:25]([CH3:26])[CH3:27])[CH2:23][O:22][C:21]3=[O:28])[CH:17]=[CH:16][N:15]=2)[CH3:4])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 86730137HCID 86730137, compoundHCID 86730265HCID 86730265, compound

Product 1

HCID 86730160(S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-oneYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-(4-(1-aminoethyl)phenyl)methanol hydrochloride (4.0301 g, 21.47 mmol, purchased from NetChem), (S)-3-(2-fluoropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (5.3648 g, 23.82 mmol, 1.11 equiv) and DIPEA (38.0 mL, 218 mmol, 10.1 equiv) in DMSO (40 mL) was heated at 110° C. for 135 min. The reaction mixture was diluted with EtOAc (200 mL) and washed with water (200 mL). After separation, the aqueous phase was washed with EtOAc (2×150 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/heptane 30 to 100%) provided (S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (6.42 g) in 84% yield.

Workup

  1. washwashed with water (200 mL)
  2. customAfter separation
  3. washthe aqueous phase was washed with EtOAc (2×150 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bf027f1da5f64a7fb5a137cba06aa09d
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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