Diisopropylethylamine → HCID 86730180, compound

HRID 1850143Notes

Reaction equation

HRID 1850143 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1.Cl.C[NH:19][CH2:20][C:21]#[CH:22].[CH:23](N(C(C)C)CC)(C)C>CS(C)=O.CCOC(C)=O>[CH:13]([C@H:12]1[CH2:11][O:10][C:9](=[O:16])[N:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:19][C@@H:20]([CH3:23])[C:21]#[CH:22])[N:7]=1)([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 22416630HCID 22416630, compoundHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Product 1

HCID 86730180HCID 86730180, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound (S)-3-(2-Chloro-pyrimidin-4-yl)-4-isopropyl-oxazolidin-2-one (1.03 g, 4.3 mmol) in DMSO (12 mL) was added methyl-prop-2-ynylamine HCl salt (450 mg, 4.3 mmol) and diisopropylethylamine (2.2 mL, 12.6 mmol). The reaction was heated to 110 C for 18 hours. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (25 mL) and brine (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified on silica gel column chromatography (EtOAc/Heptane 0 to 75%) provided (S)-4-Isopropyl-3-[2-((S)-1-methyl-prop-2-ynylamino)-pyrimidin-4-yl]-oxazolidin-2-one (360 mg) in 31% yield. LC-MS m/z: 275.1 (M−Boc)+; RT.: 1.33 min.

Workup

  1. temperatureThe reaction was heated to 110 C for 18 hours
  2. washwashed with water (25 mL) and brine (25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified on silica gel column chromatography (EtOAc/Heptane 0 to 75%)

Sources & evidence

ORD record
ord-259f04e011174aee9ae63a5f71dad13e
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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