(S)-1,1,1-trifluoropropan-2-amine → 6-Chloro-2-pyrazin-2-yl-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine

HRID 1295684

反応式

HRID 1295684 の反応式
[Cl:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=2[F:16])=[C:6](Cl)[N:5]=[C:4]([C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)[N:3]=1.[F:24][C:25]([F:30])([F:29])[C@@H:26]([NH2:28])[CH3:27]>CN1CCCC1=O.CC(O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)[N:5]=[C:6]([NH:28][C@@H:26]([CH3:27])[C:25]([F:30])([F:29])[F:24])[C:7]=1[C:8]1[C:9]([F:16])=[CH:10][C:11]([F:15])=[CH:12][C:13]=1[F:14]

参加物

6

反応物 2

HCID 10964447(S)-1,1,1-trifluoropropan-2-amineHCID 589101014,6-Dichloro-2-(pyrazin-2-yl)-5-(2,4,6-trifluorophenyl)pyrimidine

生成物 1

HCID 112819276-Chloro-2-pyrazin-2-yl-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine収率 84%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
110 °C

実験手順

To 4,6-dichloro-2-pyrazin-2-yl-5-(2,4,6-trifluoro-phenyl)-pyrimidine (40 g, 0.112 mol) in 1-methyl-2-pyrrolidinone (40 mL) there is added (S)-2,2,2-trifluoro-1-methyl-ethylamine (31.6 g, 0.28 mol). The mixture is sealed and heated to 110° C. and stirred for 24 h. The reaction mixture is cooled to room temperature and diluted with IPA (120 mL) and water (120 mL) added slowly over 30 minutes to form a solid. The solid is filtered and washed with water (2×60 mL) to give 6-chloro-2-pyrazin-2-yl-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine in 84% yield and having a 98% HPLC purity and an enantiomeric excess of >99%. 1H NMR (DMSO-D6): 9.58 (d, 1H, J=1.1 Hz), 8.85 (m, 2H), 7.72 (d, 1H, J=8.8 Hz), 7.49 (m, 2H), 5.52 (m, 1H), 1.35 (d, 3H, J=7.0 Hz).

後処理

  1. customThe mixture is sealed
  2. temperatureThe reaction mixture is cooled to room temperature
  3. additionadded slowly over 30 minutes
  4. customto form a solid
  5. filtrationThe solid is filtered
  6. washwashed with water (2×60 mL)

出典と根拠

ORDレコード
ord-2163acc7640b4640832474d866b87d71
出典データセット
uspto-grants-2007_07
特許番号
US07244736B2

関連ノート

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