Potassium Carbonate → 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)-4-Fluorobenzonitrile

HRID 1399512

반응식

HRID 1399512 반응식
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([Cl:9])[NH:4][C:3]1=[O:10].Br[CH2:12][C:13]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[Cl:9][C:5]1[N:4]([CH2:12][C:13]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:14]=2[C:15]#[N:16])[C:3](=[O:10])[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 961416-chloro-3-methylpyrimidine-2,4(1H,3H)-dioneHCID 219849902-(Bromomethyl)-4-fluorobenzonitrile

생성물 1

HCID 230893582-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)-4-Fluorobenzonitrile수율 60%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
60 °C

실험 절차

A mixture of crude 3-methyl-6-chlorouracil (5) (0.6 g, 3.8 mmol), 2-Bromomethyl-4-fluorobenzonitrile (0.86 g, 4 mmol) and K2CO3 (0.5 g, 4 mmol) in DMSO (10 mL) was stirred at 60° C. for 2 hours. The reaction was diluted with water and extracted with EtOAc. The organics were dried over MgSO4 and the solvent removed. The residue was purified by column chromatography. 0.66 g of the product was obtained (yield: 60%). 1H-NMR (400 MHz, CDCl3): δ 7.73 (dd, J=7.2, 8.4 Hz, 1H), 7.26 (d, J=4.0 Hz, 1H), 7.11-7.17 (m, 1H), 6.94 (dd, J=2.0, 9.0 Hz, 1H), 6.034 (s, 2H), 3.39 (s, 3H). MS (ES) [m+H] calc'd for C13H9ClFN3O2, 293.68; found 293.68.

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe organics were dried over MgSO4
  3. customthe solvent removed
  4. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-d7dbf829c258459787a13d80acac640d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906901B2

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