Iodoethane → HCID 178462633, 화합물

HRID 1405982노트

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HRID 1405982 반응식
[F:1][C:2]1[C:3](/[N:9]=[CH:10]/[N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[H-].[Na+].C(=S)=S.I[CH2:20][CH3:21]>CN(C=O)C>[CH2:20]([N:6]1[CH:7]=[C:2]([F:1])[C:3](/[N:9]=[CH:10]/[N:11]([CH3:13])[CH3:12])=[N:4][C:5]1=[O:8])[CH3:21]

참가 물질

6

반응물 4

HCID 6340IodoethaneHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 178484256HCID 178484256, 화합물

생성물 1

HCID 178462633HCID 178462633, 화합물수율 91.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

A 25 mL screw-top vial was charged with (E)-N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformimidamide (99.5 mg, 0.540 mmol), DMF (2 mL), and NaH (60% dispersion in mineral oil; 24.5 mg, 0.613 mmol) and was agitated on a rotary shaker at 50° C. for 40 min. After cooling to room temperature, carbon disulfide (0.036 mL, 0.599 mmol) was added, and the reaction mixture was agitated on a rotary shaker at room temperature for 90 min. At this point, iodoethane (0.052 mL, 0.650 mmol) was added, and the reaction mixture was further agitated at room temperature for 3.5 h, whereupon the crude mixture was concentrated in vacuo. The crude material was purified by normal phase chromatography (gradient, 0 to 30% MeOH/CH2Cl2) to afford (E)-N′-(1-ethyl-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)-N,N-dimethylformimidamide (105 mg, 67%) as a white solid: mp 157-160° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.62 (s, 1H), 8.09 (d, J=6.2 Hz, 1H), 3.70 (q, J=7.1 Hz, 2H), 3.20 (s, 3H), 3.07 (s, 3H), 1.18 (t, J=7.1 Hz, 3H); ESIMS m/z 213 ([M+H]+.

후처리

  1. temperatureAfter cooling to room temperature
  2. stirringthe reaction mixture was agitated on a rotary shaker at room temperature for 90 min
  3. concentrationwas concentrated in vacuo
  4. customThe crude material was purified by normal phase chromatography (gradient, 0 to 30% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-f110e051a1c748e295ed3b0d6f69e22c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916579B2

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