Sodium Hydroxide → 7-(1-bromoethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 58235

반응식

HRID 58235 반응식
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[Br:8][CH:9]([CH3:17])[C:10](=O)[CH2:11][C:12](OC)=[O:13].[OH-].[Na+]>C(Cl)Cl>[Br:8][CH:9]([C:10]1[N:7]=[C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]2[C:12](=[O:13])[CH:11]=1)[CH3:17]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 741432-Amino-4-methylthiazoleHCID 9815681Methyl 4-bromo-3-oxopentanoate

생성물 1

HCID 581114377-(1-bromoethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one수율 42.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
110 °C

실험 절차

To a manually stirred polyphosphoric acid (80 g, 800 mmol) in a 1000 mL beaker was added 4-methyl-1,3-thiazol-2-amine (Aldrich, 16 g, 140 mmol), followed by methyl 4-bromo-3-oxopentanoate (34.9 g, 167 mmol). The mixture was heated with stirring at 110° C. for 5 h. After cooling, the dark slurry was transferred into 300 g of ice. The pH of the mixture was adjust to 6-7 with 10% sodium hydroxide. The aqueous layer was discarded and the dark oil layer was diluted with methylene chloride and washed with 1 N NaOH, brine, dried over magnesium sulfate, and evaporated to dryness to yield the desired product (16.2 g, 42.6%). LCMS calculated for C9H10BrN2OS (M+H)+: m/z=273.0. Found: 273.1.

후처리

  1. temperatureThe mixture was heated
  2. temperatureAfter cooling
  3. washwashed with 1 N NaOH, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-3d39cbf6fe72471980f6ce7c68113188
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434746B2

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