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Water → 2-(4-Methoxy-3,5-dimethylphenyl)-5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidine

HRID 403462
ノート
印刷プレビュー

反応式

HRID 403462 の反応式
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:20][CH3:21])[N:15]=[C:16]([OH:19])[C:17]=3[N:18]=2)=[CH:5][C:4]=1[CH3:22].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH3:32].O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[CH:5][C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:20][CH3:21])[N:15]([CH2:30][CH2:31][CH3:32])[C:16](=[O:19])[C:17]=3[N:18]=2)=[CH:7][C:8]=1[CH3:9].[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[CH:5][C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:20][CH3:21])[N:15]=[C:16]([O:19][CH2:30][CH2:31][CH3:32])[C:17]=3[N:18]=2)=[CH:7][C:8]=1[CH3:9]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 178489873HCID 178489873、化合物

生成物 2

HCID 672941732-(4-Methoxy-3,5-dimethylphenyl)-5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidineHCID 67294209HCID 67294209、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

5.9 g of 2-(4-methoxy-3,5-dimethyl-phenyl)-5-methylsulfanyl-oxazolo[5,4-d]pyrimidin-7-ol were dissolved in 150 ml of N,N-dimethylformamide, and 7.7 g of potassium carbonate and then 2.7 g of 1-bromo-propane were added. The solution was stirred at 60° C. for 5 h and then, after cooling, poured onto 150 ml of water. The precipitate was filtered off with suction. The obtained mixture of regioisomers was purified by silica gel chromatography (50 g silica (solute cartridge, heptane/ethyl acetate 9/1). Besides 1.4 g of 2-(4-methoxy-3,5-dimethyl-phenyl)-5-methylsulfanyl-6-propyl-6H-oxazolo[5,4-d]pyrimidin-7-one (LC/MS (method LC1): Rt=1.43 min; m/z=360.13 [M+H]+), 2.5 g of the title compound were obtained.

後処理

  1. temperatureafter cooling
  2. filtrationThe precipitate was filtered off with suction
  3. additionThe obtained mixture of regioisomers
  4. customwas purified by silica gel chromatography (50 g silica (solute cartridge, heptane/ethyl acetate 9/1)

出典と根拠

ORDレコード
ord-0994a361c85c4b329b52a1a3e56c1541
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748436B2

反応ノート

読み込み中…

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