4,6-Bis(1,1-dimethylethyl)-5-hydroxy-N-methoxy-N-methyl-2-pyrimidinecarboxamide → 1-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-1-propanone

HRID 1033759노트

반응식

HRID 1033759 반응식
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([C:16](N(OC)C)=[O:17])[N:6]=1)([CH3:4])[CH3:3].[CH2:22]([Mg]Br)[CH3:23]>O1CCCC1.C(OCC)C>[CH3:13][C:12]([C:9]1[C:10]([OH:11])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:6]=[C:7]([C:16](=[O:17])[CH2:22][CH3:23])[N:8]=1)([CH3:14])[CH3:15]

참가 물질

5

반응물 2

HCID 100401704,6-Bis(1,1-dimethylethyl)-5-hydroxy-N-methoxy-N-methyl-2-pyrimidinecarboxamideHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 104229331-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-1-propanone

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 8.4 g (28 mmol) of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-N-methoxy-N-methyl-2-pyrimidinecarboxamide in 150 mL of tetrahydrofuran was cooled in ice and treated dropwise with 40 mL (120 mmol) of a 3.0 M solution of ethylmagnesium bromide in diethyl ether. The mixture was stirred in ice for 2 hours, then at room temperature for an additional 16 hours. The reaction mixture was again cooled in ice, and excess Grignard reagent was destroyed by dropwise addition of 50 mL of saturated aqueous ammonium chloride solution. The reaction mixture was added to 400 mL of ammonium chloride solution and extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried (anhydrous sodium sulfate), and evaporated. Recrystallization of the residue from hexane yielded 5.0 g (67%) of the ethyl ketone product, mp 123° C. -125° C.

후처리

  1. waitat room temperature for an additional 16 hours
  2. temperatureThe reaction mixture was again cooled in ice
  3. customexcess Grignard reagent was destroyed by dropwise addition of 50 mL of saturated aqueous ammonium chloride solution
  4. additionThe reaction mixture was added to 400 mL of ammonium chloride solution
  5. extractionextracted several times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (anhydrous sodium sulfate)
  8. customevaporated
  9. customRecrystallization of the residue from hexane
  10. customyielded 5.0 g (67%) of the ethyl ketone product, mp 123° C. -125° C.

출처 및 근거

ORD 기록
ord-83cb07ac8eed41129e04b9b768fdbedb
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05312821

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