Diisopropylethylamine → HCID 90415155、化合物

HRID 57365

反応式

HRID 57365 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 90415155HCID 90415155、化合物収率 73.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0ab06965daa840248da2aaa4a13a53e8
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

関連ノート

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