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Diisopropylethylamine → Methyl 4-(2-chloro-5-nitropyrimidin-4-yl)-3-methylmorpholine-3-carboxylate

HRID 2386235
ノート
印刷プレビュー

反応式

HRID 2386235 の反応式
[CH3:1][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:12][C:13]1[N:18]=[C:17]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][C:2]2([CH3:1])[C:8]([O:10][CH3:11])=[O:9])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=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 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 67268303Methyl 3-methylmorpholine-3-carboxylate

生成物 1

HCID 78165341Methyl 4-(2-chloro-5-nitropyrimidin-4-yl)-3-methylmorpholine-3-carboxylate収率 100.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

Methyl 3-methylmorpholine-3-carboxylate (4.21 g, 26.4 mmol) was dissolved in THF (60 ml) to form a clear solution. 2,4-Dichloro-5-nitropyrimidine (5.13 g, 26.4 mmol) was added and the solution was cooled to −10° C. Diisopropylethylamine (6.93 ml, 39.7 mmol) was added while the temperature was maintained at −8 to −10° C. The reaction was stirred for 4 hours at 0° C. and for 16 hours at room temperature. The solvent was removed under reduced pressure. EtOAc (120 ml) was added and the mixture was washed with water (3×30 ml). The organic solution was concentrated to afford 8.4 g of crude methyl 4-(2-chloro-5-nitropyrimidin-4-yl)-3-methylmorpholine-3-carboxylate as an oil. The crude material was used in the next step without further purification. MS [M+H] calculated for C11H13ClN4O5, 317. found, 317

後処理

  1. customto form a clear solution
  2. temperaturewas maintained at −8 to −10° C
  3. customThe solvent was removed under reduced pressure
  4. additionEtOAc (120 ml) was added
  5. washthe mixture was washed with water (3×30 ml)
  6. concentrationThe organic solution was concentrated

出典と根拠

ORDレコード
ord-6c41b933fc48427680b71f17f3ed395d
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08268819B2

反応ノート

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