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

HRID 2234937ノート

反応式

HRID 2234937 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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+]

後処理

  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

出典と根拠

ORDレコード
ord-e54e7a97abf549f1bb51538fe52aed25
出典データセット
uspto-grants-2010_05
特許番号
US07713982B2

反応ノート

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