Diisopropylethylamine → HCID 90415155, compound

HRID 57365

Reaction equation

HRID 57365 reaction equation
[NH2:1][C@@H:2]([C@@H:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:6])[CH2:3][OH:4].[F:12][C:13]1[N:18]=[C:17](F)[C:16]([F:20])=[CH:15][N:14]=1.CCN(C(C)C)C(C)C>C(#N)C>[C:8]([O:7][C@@H:5]([CH3:6])[C@H:2]([NH:1][C:15]1[C:16]([F:20])=[CH:17][N:18]=[C:13]([F:12])[N:14]=1)[CH2:3][OH:4])([CH3:10])([CH3:9])[CH3:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 127973072,4,5-TrifluoropyrimidineHCID 90414285(2R,3S)-2-amino-3-(tert-butoxy)butan-1-ol

Product 1

HCID 90415155HCID 90415155, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a round bottom flask containing (2R,3S)-2-amino-3-(tert-butoxy)butan-1-ol (1.25 g, 7.75 mmol) and a stir bar was added acetonitrile (50 mL) followed by the addition of 2,4,5-trifluoropyrimidine (1.04 g, 7.75 mmol) and DIEA (4.1 mL, 23.3 mmol). The resulting reaction mixture allowed to stir 1 hr at room temperature. The volatiles were then removed. Reaction mixture was then partitioned between EtOAc and water. Aqueous layer extracted with EtOAc. Organic phases combined, washed with water, brine, dried (Na2SO4), filtered and concentrated to a viscous yellow oil of (2R,3S)-3-(tert-butoxy)-2-((2,5-difluoropyrimidin-4-yl)amino)butan-1-ol (1.56 g, 5.67 mmol, 73% yield). 1H NMR (400 MHz, CDCl3) δ 1.15 (s, 9H) 1.32 (d, J=6.26 Hz, 3H) 3.45 (br. s., 1H) 3.67 (d, J=11.35 Hz, 1H) 3.85-3.92 (m, 1H) 4.27 (d, J=11.74 Hz, 1H) 6.29 (d, J=5.48 Hz, 1H) 7.87 (d, J=2.35 Hz, 1H). LCMS m/z 276.4 (M+H)+, Rt 0.71 min.

Workup

  1. customThe resulting reaction mixture
  2. customThe volatiles were then removed
  3. customReaction mixture
  4. customwas then partitioned between EtOAc and water
  5. extractionAqueous layer extracted with EtOAc
  6. washwashed with water, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-0ab06965daa840248da2aaa4a13a53e8
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Linked notes

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