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 1033759ノート

反応式

HRID 1033759 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-83cb07ac8eed41129e04b9b768fdbedb
出典データセット
uspto-grants-1994_05
特許番号
US05312821

反応ノート

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