Diethyl Ether → 4-(5-Trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyraldehyde

HRID 12659

反応式

HRID 12659 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9](=[O:16])[NH:8][C:7]1=[O:17].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC>C1COCC1>[F:14][C:12]([F:13])([F:15])[C:10]1[C:9](=[O:16])[NH:8][C:7](=[O:17])[N:6]([CH2:5][CH2:4][CH2:3][CH:2]=[O:1])[CH:11]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 589942241-(4-Hydroxy-butyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

生成物 1

HCID 589941974-(5-Trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyraldehyde収率 51.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

1-(4-Hydroxy-butyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione (Prep 23, 44 mg, 0.17 mmol) was dissolved in dry THF (5 mL), the solution was cooled to 0° C. and Dess-Martin periodinane (127 mg, 0.28 mmol) was added. The mixture was stirred at 0° C. for 1.5 hours. Et2O was added and the solution washed with aqueous saturated NaHCO3. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-1) to give 22 mg of the title compound (50% yield).

後処理

  1. washthe solution washed with aqueous saturated NaHCO3
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-1)

出典と根拠

ORDレコード
ord-2d9ddf4e5bc948ea8390a84b8afb5556
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

関連ノート

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