Diisopropylethylamine → HCID 90415155, 화합물

HRID 57365

반응식

HRID 57365 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 90415155HCID 90415155, 화합물수율 73.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ab06965daa840248da2aaa4a13a53e8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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