Hydrochloric Acid → 5-Fluoro-4-(4-fluoro-2-methoxyphenyl)-N-{3-[(methylsulfanyl)methyl]phenyl}pyrimidin-2-amine

HRID 2277749ノート

反応式

HRID 2277749 の反応式
Cl.O1CCOCC1.Cl[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[O:22][CH3:23])[C:12]([F:24])=[CH:11][N:10]=1.[CH3:25][S:26][CH2:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)[NH2:31]>C(O)CCC.C(OCC)(=O)C>[F:24][C:12]1[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[O:22][CH3:23])=[N:14][C:9]([NH:31][C:30]2[CH:32]=[CH:33][CH:34]=[C:28]([CH2:27][S:26][CH3:25])[CH:29]=2)=[N:10][CH:11]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 397333593-[(Methylsulfanyl)methyl]anilineHCID 867296092-Chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine

生成物 1

HCID 894443955-Fluoro-4-(4-fluoro-2-methoxyphenyl)-N-{3-[(methylsulfanyl)methyl]phenyl}pyrimidin-2-amine収率 72.2%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

A 4N solution of hydrogen chloride in dioxane (0.61 mL; 2.45 mmol) was added to a stirred solution of 2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine (630 mg; 2.45 mmol) and 3-[(methyl-sulfanyl)methyl]aniline (564 mg; 3.68 mmol) in 1-butanol (5.4 mL). The batch was stirred at 140° C. for 16 hours. After cooling the batch was diluted with ethyl acetate and washed with aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic phase was filtered using a Whatman filter and concentrated. The residue was purified by chromatography (hexane/ethyl acetate 2:1) to give the desired product (662 mg; 1.77 mmol).

後処理

  1. temperatureAfter cooling the batch
  2. washwashed with aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  3. filtrationThe organic phase was filtered
  4. filtrationfilter
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (hexane/ethyl acetate 2:1)

出典と根拠

ORDレコード
ord-57844259a38f41d4ad8be1906f9a8075
出典データセット
uspto-grants-2015_09
特許番号
US09133171B2

反応ノート

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