2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine → 2-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-5-methyl-1H-pyrimidin-4-one

HRID 474879

反応式

HRID 474879 の反応式
[CH3:1][C:2]1[C:3](=[O:10])[N:4]=[C:5](SC)[NH:6][CH:7]=1.[Cl:11][C:12]1[CH:27]=[CH:26][C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH2:25])=[CH:19][CH:18]=2)=[CH:14][C:13]=1[C:28]([F:31])([F:30])[F:29]>C(O)C>[Cl:11][C:12]1[CH:27]=[CH:26][C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH:25][C:5]3[NH:6][CH:7]=[C:2]([CH3:1])[C:3](=[O:10])[N:4]=3)=[CH:19][CH:18]=2)=[CH:14][C:13]=1[C:28]([F:29])([F:30])[F:31]

参加物

4

反応物 2

HCID 677755482-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamineHCID 178503551HCID 178503551、化合物

生成物 1

HCID 1784308912-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-5-methyl-1H-pyrimidin-4-one収率 35.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

5-Methyl-2-methylsulfanyl-1H-pyrimidin-4-one (25 mg, 0.16 mmol, 1 eq) and 2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (60 mg, 0.192 mmol, 1.2 eq) were stirred in 300 μl of absolute ethanol for 50 hours. Solvent was then evaporated and the resulting crude was purified by chromatography on BIOTAGE SP1 purification device using 11 g normal phase silica KP-NH column and DCM/MeOH solvent system (gradient 0-7% of MeOH in 20 column volumes). Solvent from the gathered fractions of appropriate composition was evaporated and the crude was triturated with cyclohexane to obtain 2-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-5-methyl-1H-pyrimidin-4-one (24 mg, yield=33.9%, purity=96%) in form of white powder. MS: [M+H]+=424.31. 1H NMR (300 MHz; CDCl3) δ/ppm 1.79 (s, 3H), 2.90 (t, J=6.24 Hz, 2H), 3.52 (s, 2H), 3.56-3.67 (m, 2H), 6.23 (br.s., 1H), 6.92 (d, J=7.56 Hz, 2H), 7.00 (d, J=7.95 Hz, 1H), 7.21 (d, J=7.56 Hz, 2H), 7.28 (s, 1H) 7.38 (d, J=8.32 Hz, 1H), 7.63 (s, 1H), 11.62 (br.s., 1H).

後処理

  1. customSolvent was then evaporated
  2. customthe resulting crude was purified by chromatography on BIOTAGE SP1 purification device
  3. customSolvent from the gathered fractions of appropriate composition was evaporated
  4. customthe crude was triturated with cyclohexane

出典と根拠

ORDレコード
ord-be184099834742dfa61f92e7104993ad
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

関連ノート

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