Iodoethane → HCID 178462633、化合物

HRID 1405982ノート

反応式

HRID 1405982 の反応式
[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]

参加物

6

反応物 4

HCID 6340IodoethaneHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 178484256HCID 178484256、化合物

生成物 1

HCID 178462633HCID 178462633、化合物収率 91.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-f110e051a1c748e295ed3b0d6f69e22c
出典データセット
uspto-grants-2014_12
特許番号
US08916579B2

反応ノート

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