Dimethylformamide → 1-Methyl-2,6-dioxo-3-pentyl-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbaldehyde

HRID 2234937노트

반응식

HRID 2234937 반응식
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8]([CH2:12][CH:13]=[CH2:14])[CH:7]=[N:6][C:5]=2[N:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]1=[O:20].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CN([CH:34]=[O:35])C>C1COCC1>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8]([CH2:12][CH:13]=[CH2:14])[C:7]([CH:34]=[O:35])=[N:6][C:5]=2[N:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]1=[O:20]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 2733832Lithium HexamethyldisilazideHCID 592995971-methyl-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

생성물 1

HCID 592995531-Methyl-2,6-dioxo-3-pentyl-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbaldehyde수율 30%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 1-methyl-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (1.05 g, 3.6 mmol) in THF (15 ml) at −78° C. was added LiHMDS (4 ml, 1M in hexane, 4 mmol) over 10 min and the solution stirred for 0.5 h. DMF (0.5 ml) was added and the solution stirred at −78° C. for a further 0.5 h then allowed to warm to ambient temperature with the cooling bath over 2 h. The reaction was quenched with 2N hydrochloric acid (3 ml) and partioned between ethyl acetate and brine. The organics were isolated, dried and concentrated. The crude product was chomatographed over silica (gradient elution dichloromethane to 5:1 dichloromethane/ethyl acetate) to afford the title compound as a white solid (0.35 g, 30%). m/z 305[MH+]

후처리

  1. stirringthe solution stirred at −78° C. for a further 0.5 h
  2. customThe reaction was quenched with 2N hydrochloric acid (3 ml)
  3. customThe organics were isolated
  4. customdried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e54e7a97abf549f1bb51538fe52aed25
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713982B2

반응 노트

불러오는 중…