4-Nitrophenyl chloroformate → 5-Methyl 1-(4-nitrophenyl) 6-(4-fluorophenyl)-2-methoxy-4-methyl-1,5(6H)-pyrimidinedicarboxylate

HRID 1452655ノート

反応式

HRID 1452655 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:13][C:12]([O:14][CH3:15])=[N:11][C:10]([CH3:16])=[C:9]2[C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:13]([C:22]([O:24][C:25]3[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=3)=[O:23])[C:12]([O:14][CH3:15])=[N:11][C:10]([CH3:16])=[C:9]2[C:17]([O:19][CH3:20])=[O:18])=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 821294-Nitrophenyl chloroformateHCID 178498443HCID 178498443、化合物

生成物 1

HCID 105272225-Methyl 1-(4-nitrophenyl) 6-(4-fluorophenyl)-2-methoxy-4-methyl-1,5(6H)-pyrimidinedicarboxylate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of methyl 6-(4-fluorophenyl)-2-methoxy-4-methyl-1,6-dihydro-5-pyrimidinecarboxylate (1.76 g, 6.34 mmol) and 4-dimethylaminopyridine (12.7 mmol, 1.55 g) in anhydrous CH2Cl2 (20.0 mL) was added solution of 4-nitrophenyl chloroformate (4.47 g, 22.2 mmol) in CH2Cl2 (20.0 mL) at 23° C. The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was diluted with CH2Cl2 (50 mL), washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (hexanesiethyl acetate 4:1). The product was obtained as yellow syrup, which upon trituration with hexanes became a white powder (2.40 g, 84.3%). The crude product was used in next step without further purification.

後処理

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography (hexanesiethyl acetate 4:1)
  5. customThe product was obtained as yellow syrup, which upon trituration with hexanes
  6. customThe crude product was used in next step without further purification

出典と根拠

ORDレコード
ord-e0322ba4644b49aa83d7f4108e774005
出典データセット
uspto-grants-2009_01
特許番号
US07473698B2

反応ノート

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