Methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate → 5-Benzyloxy-2-cyclohexylmethyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid methyl ester

HRID 1409596노트

반응식

HRID 1409596 반응식
[CH:1]1([CH2:7][Mg]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][O:11][C:12]([C:14]1[N:15]=[C:16](S(C)(=O)=O)[N:17]([CH3:29])[C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13]>C1COCC1>[CH3:10][O:11][C:12]([C:14]1[N:15]=[C:16]([CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:17]([CH3:29])[C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13]

참가 물질

4

반응물 2

HCID 86710287Methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylateHCID 178419664HCID 178419664, 화합물

생성물 1

HCID 867102965-Benzyloxy-2-cyclohexylmethyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid methyl ester수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Cyclohexylmethylmagnesium bromide solution (1.77 ml; 885 μM of 0.5M solution in THF) was added dropwise to a solution of 5-benzyloxy-2-methanesulfonyl-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester (0.26 g; 738 μM) in THF (10 ml). After stirring at room temperature for 1 h, the reaction mixture was quenched by the addition of saturated ammonium chloride solution. The product was extracted into EtOAc, washed with brine, dried (Na2SO4) and evaporated to dryness under reduced pressure to give the title product as a colourless oil (0.040 g; 70%). LCMS: m/z=367 (MH+).

후처리

  1. customthe reaction mixture was quenched by the addition of saturated ammonium chloride solution
  2. extractionThe product was extracted into EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-7a8cd4a0789144718e3ec847629f597e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921388B2

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