Dimethylformamide → HCID 86710192、化合物

HRID 2284430ノート

反応式

HRID 2284430 の反応式
Br[C:2]1[CH:11]=[N:10][C:9]2[C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:7][C:6]([Cl:18])=[N:5][C:4]=2[CH:3]=1.C([Li])CCC.CN(C)[CH:26]=[O:27]>C1COCC1>[Cl:18][C:6]1[N:7]=[C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[N:10]=[CH:11][C:2]([CH:26]=[O:27])=[CH:3][C:4]=2[N:5]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 86665768HCID 86665768、化合物HCID 178418339Butyllithium

生成物 1

HCID 86710192HCID 86710192、化合物収率 31.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a 50 mL round bottom flask, 4-(7-bromo-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine (3.0 g, 0.0091 mol—Preparation 3) and dry THF (15 mL) were added under nitrogen atmosphere and then cooled to −78° C. To the reaction flask, 2.5 M n-butyl lithium (4.4 mL, 0.0109 mol) was slowly added and the reaction mixture was stirred at −78° C. for 30 minutes. To the reaction mixture, N,N-dimethylformamide (1.27 mL, 0.0164 mol) was added and the reaction mixture allowed to warm to 0° C. The reaction mass was quenched with 10% aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to provide the crude product. The crude product was purified by column chromatography (60-120 silica gel, 10-40% ethyl acetate) to provide the title compound as a light yellow solid (0.8 g, 31%). 1H NMR (300 MHz, CDCl3): δ 10.24 (s, 1H), 9.11 (d, J=2.1 Hz, 1H), 8.41 (d, J=2.1 Hz, 1H), 3.91 (t, J=4.8 Hz, 8H): LC-MS (ESI): Calculated mass. 278.06, Observed mass [M+H]+: 279.0 (RT=0.66 min).

後処理

  1. temperatureto warm to 0° C
  2. customThe reaction mass was quenched with 10% aqueous ammonium chloride (100 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customto provide the crude product
  8. customThe crude product was purified by column chromatography (60-120 silica gel, 10-40% ethyl acetate)

出典と根拠

ORDレコード
ord-29429fe6c68642cdaae9119c6d219a80
出典データセット
uspto-grants-2015_09
特許番号
US09145411B2

反応ノート

読み込み中…