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4-Nitrophenyl chloroformate → 6-(4-Cyanophenyl)-2-methoxy-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 5-methyl ester 1-(4-nitrophenyl) ester

HRID 570867
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HRID 570867 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:7]=[C:8]([O:12][CH3:13])[NH:9][C:10]=1[CH3:11])=[O:4].Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24]>C(Cl)Cl.N1C=CC=CC=1>[N+:32]([C:29]1[CH:28]=[CH:27][C:26]([O:25][C:23]([N:7]2[CH:6]([C:14]3[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=3)[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:10]([CH3:11])[N:9]=[C:8]2[O:12][CH3:13])=[O:24])=[CH:31][CH:30]=1)([O-:34])=[O:33]
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참가 물질

5

반응물 2

HCID 821294-Nitrophenyl chloroformateHCID 674375874-(4-Cyanophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylic acid methyl ester

생성물 1

HCID 866782176-(4-Cyanophenyl)-2-methoxy-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 5-methyl ester 1-(4-nitrophenyl) ester

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane
용매
2회

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온도
0 °C

실험 절차

Intermediate 4 (1.56 g, 5.46 mmol) was dissolved in a mixture of DCM (25 mL) and pyridine (10 mL) and cooled using an ice bath. A solution of 4-nitrophenyl chloroformate (705 mg, 3.50 mmol) in DCM (25 mL) was added over 30 minutes. The reaction mixture was stirred for 1 hour at 0° C. and then the solvent was removed in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-20% EtOAc in cyclohexane to gave the title compound as a yellow solid. The product thus obtained was used in the subsequent step without further analysis (2.0 g).

후처리

  1. temperaturecooled
  2. customthe solvent was removed in vacuo
  3. customThe resulting residue was purified by silica gel chromatography
  4. washeluting with a gradient of 0-20% EtOAc in cyclohexane

출처 및 근거

ORD 기록
ord-341452b4ab6b4c179eb5f77f5ebecceb
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09023855B2

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