Sodium Chloride → Methyl 2,6-dichloro-5-methoxypyrimidine-4-carboxylate

HRID 332922

반응식

HRID 332922 반응식
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[C:5]([O:10][CH3:11])=[C:4]([Cl:12])[N:3]=1.[C:13](=O)(O)[O-:14].[Na+].BrBr.N1C=CC=NC=1.S(=O)(O)[O-].[Na+].[Cl-].[Na+]>CO.CO.O.O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:14][CH3:13])=[O:9])[C:5]([O:10][CH3:11])=[C:4]([Cl:12])[N:3]=1

참가 물질

10

반응물 6

HCID 5234Sodium ChlorideHCID 9260PyrimidineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 866893302,6-Dichloro-5-methoxypyrimidine-4-carbaldehyde

생성물 1

HCID 11514203Methyl 2,6-dichloro-5-methoxypyrimidine-4-carboxylate수율 87%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 22242641Methanol--water (1/1)용매

실험 절차

A solution of 2,6-dichloro-5-methoxy-pyrimidine-4-carbaldehyde (see Examples 6 and 7 above for methods for preparing this compound) (50 g, 0.24 mol) in methanol (1 L) and water (60 mL) was prepared. To the solution, sodium bicarbonate (400 g) was added. A 2 M solution of bromine (192 g, 1.2 mol) in methanol/water (600 mL, 9:1) was added, dropwise, to the pyrimidine solution for 45 minutes at 0° C. while stirring the mixture. The stirring was continued at the same temperature for 1 h. Later, the mixture was stirred at room temperature for 4 h. While stirring, the reaction mixture was thereafter poured onto a mixture of crushed ice (2 L), sodium bisulfite (50 g), and sodium chloride (200 g). The product was extracted with ethyl acetate (1 L×2), and the combined organic layer was dried over sodium sulfate and filtered. Evaporation of the solvent under reduced pressure produced a thick material, which was then solidified on long standing. This produced the title compound (50.8 g, 87% yield); LC-MS 238 (m+1); HPLC (95% acetonitrile buffered with 0.1% v/v acetic acid.

후처리

  1. stirringWhile stirring
  2. extractionThe product was extracted with ethyl acetate (1 L×2)
  3. dry with materialthe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customEvaporation of the solvent under reduced pressure
  6. customproduced a thick material, which

출처 및 근거

ORD 기록
ord-7b1236b8e8994b1e8e1a34a25140593f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877925B2

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