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Ethyl bromoacetate → Ethyl 2-(4,6-dimethyl-5-nitropyrimidine-2-yloxy)acetate

HRID 2280888
ノート
印刷プレビュー

反応式

HRID 2280888 の反応式
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[N:5]=[C:4]([OH:12])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O>[CH3:11][C:6]1[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[N:3]=[C:4]([O:12][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:5]=1
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

5

反応物 3

HCID 7748Ethyl bromoacetate2 回HCID 11430Potassium CarbonateHCID 178433502HCID 178433502、化合物

生成物 1

HCID 59336196Ethyl 2-(4,6-dimethyl-5-nitropyrimidine-2-yloxy)acetate収率 45%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
50 °C

実験手順

Compound 1 (111.86 g) and potassium carbonate (274.21 g: 3 eq.) were suspended in acetone (2 L) and ethyl bromoacetate (165.67 g: 1.5 eq.) was added at room temperature (20 to 30° C.). The equipment used to add ethyl bromoacetate was thoroughly washed with acetone (237 mL) and stirred at 50° C. for 8 hours. Subsequently, the mixture was cooled to 35° C. and was concentrated under reduced pressure. To the resulting residue, toluene (1120 mL) was added and the mixture was stirred at room temperature overnight. The mixture was then suction-filtered and the filtered product was washed with toluene (560 mL). The filtered product was crushed and washed again with toluene (450 mL). The filtrate was evaporated under reduced pressure and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=1:0 to 4:1) to give 75.98 g (45% yield) of the desired product as a yellow solid.

後処理

  1. washwas thoroughly washed with acetone (237 mL)
  2. temperatureSubsequently, the mixture was cooled to 35° C.
  3. concentrationwas concentrated under reduced pressure
  4. additionTo the resulting residue, toluene (1120 mL) was added
  5. stirringthe mixture was stirred at room temperature overnight
  6. filtrationThe mixture was then suction-filtered
  7. washthe filtered product was washed with toluene (560 mL)
  8. customThe filtered product was crushed
  9. washwashed again with toluene (450 mL)
  10. customThe filtrate was evaporated under reduced pressure
  11. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=1:0 to 4:1)

出典と根拠

ORDレコード
ord-8e250a6175ad4d449de56131758f4f24
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09139559B2

反応ノート

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