Potassium Bicarbonate → HCID 52206516、化合物

HRID 530094ノート

反応式

HRID 530094 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][CH:13]([CH3:23])[CH2:14][CH2:15][NH:16][C@H:17]([C:19]([O:21][CH3:22])=[O:20])[CH3:18].C(=O)(O)[O-].[K+]>CCOCC>[Cl:1][C:2]1[N:7]=[C:6]([N:16]([CH2:15][CH2:14][CH:13]([CH3:23])[CH3:12])[C@H:17]([C:19]([O:21][CH3:22])=[O:20])[CH3:18])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 43230241HCID 43230241、化合物

生成物 1

HCID 52206516HCID 52206516、化合物収率 51%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A solution of 2,4-dichloro-5-nitropyrimidine (27.8 g, 144 mmol) in ether (350 mL) was cooled to −10° C. and was treated with methyl N-(3-methylbutyl)alaninate (20.8 g, 120 mmol). A solution of potassium bicarbonate (25.0 g in 180 mL water) was added drop wise maintaining the temperature below 0° C. Reaction mixture was then allowed to come to room temperature and stirred for 2 h. Ether layer was separated, the aq. layer was extracted with ether (3×100 mL). Combined ether solution was washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by flash chromatography on silica gel using ethyl acetate-hexane mixture (v:v=5:95) to give titled product (yield: 51%). 1HNMR (300 MHz, CDCl3): δ 0.90-1.01 (m, 6H), 1.40-1.61 (m, 6H), 3.10-3.21 (m, 1H), 3.39-3.45 (m, 1H), 3.78 (s, 3H), 4.41-4.50 (s, 1H), 8.71 (s, 1H).

後処理

  1. temperaturewise maintaining the temperature below 0° C
  2. customReaction mixture
  3. customto come to room temperature
  4. customEther layer was separated
  5. extractionthe aq. layer was extracted with ether (3×100 mL)
  6. washCombined ether solution was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-3b05e0a33dac42fdb59078e834350f3b
出典データセット
uspto-grants-2016_05
特許番号
US09351974B2

反応ノート

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