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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Carbamimidic acid, methyl ester, sulfate (1:1) → 1,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester

HRID 1722405
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인쇄 미리보기

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HRID 1722405 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:17](=O)[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:20][O:21][C:22]([NH2:24])=[NH:23].OS(O)(=O)=O.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[CH3:20][O:21][C:22]1[NH:24][C:17]([CH3:18])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:23]=1
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참가 물질

6

반응물 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 367507Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoateHCID 516892Sodium Bicarbonate

생성물 1

HCID 139125831,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester수율 61.6%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

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온도
70 °C

실험 절차

A mixture of 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, ethyl ester (16.46 g, 62.6 mmol), o-methylisourea hydrogen sulfate (14.00 g, 81.4 mmol), and sodium bicarbonate (15.8 g, 18.8 mmol) in dimethylformamide (9.4 ml) was heated at 70° C. (oil bath) under argon overnight. The cooled reaction was diluted with water and extracted with ethyl acetate. The organic phase was washed several times with water, washed with saturated sodium chloride, dried (potassium carbonate) and evaporated. The residue was passed through a pad of silica gel, crystallized from isopropyl ether/hexanes and then triturated with 60% isopropyl ether hexanes (50 ml) to give 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester as light yellow crystals (12.32 g), melting point 101°-103° C.

후처리

  1. customThe cooled reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed several times with water
  4. washwashed with saturated sodium chloride
  5. dry with materialdried (potassium carbonate)
  6. customevaporated
  7. customcrystallized from isopropyl ether/hexanes
  8. customtriturated with 60% isopropyl ether hexanes (50 ml)

출처 및 근거

ORD 기록
ord-257e0764e31c455cb1d0026f6434a4c1
출처 데이터셋
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04855301

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