Acetonitrile → 2-Amino-3-{4-[6-(2,2,2-trifluoro-1-phenyl-ethoxy)-pyrimidin-4-yl]-phenyl}-propionic acid

HRID 254756

反応式

HRID 254756 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([F:13])([F:12])[F:11])[N:5]=[CH:4][N:3]=1.B([C:23]1[CH:34]=[CH:33][C:26]([CH2:27][C@@H:28]([C:30]([OH:32])=[O:31])[NH2:29])=[CH:25][CH:24]=1)(O)O.C(#N)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:29][CH:28]([CH2:27][C:26]1[CH:33]=[CH:34][C:23]([C:2]2[CH:7]=[C:6]([O:8][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([F:13])([F:12])[F:11])[N:5]=[CH:4][N:3]=2)=[CH:24][CH:25]=1)[C:30]([OH:32])=[O:31]

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 150315L-p-BoronophenylalanineHCID 866143014-Chloro-6-(2,2,2-trifluoro-1-phenyl-ethoxy)-pyrimidine

生成物 1

HCID 666492722-Amino-3-{4-[6-(2,2,2-trifluoro-1-phenyl-ethoxy)-pyrimidin-4-yl]-phenyl}-propionic acid収率 11,500.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

An Emrys process vial (2-5 ml) for microwave was charged with 4-chloro-6-(2,2,2-trifluoro-1-phenyl-ethoxy)-pyrimidine (30 mg, 0.1 μmol), 4-borono-L-phenylalanine (32 mg, 0.16 mmol), 1 ml of acetonitrile and 0.6 ml of water. Aqueous sodium carbonate (0.42 ml, 1M) was added to above solution followed by 10 mol percent of POPd2 (dihydrogen di-μ-chlorodichlorobis(di-tert-butylphosphinito-κP)dipalladate. The reaction vessel was sealed and heated to 120° C. for 30 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, and the product was purified with Prep-LC to give 4.8 mg of 2-amino-3-{4-[6-(2,2,2-trifluoro-1phenyl-ethoxy)-pyrimidin-4-yl]-phenyl}-propionic acid, yield 11%. 1H-NMR (400 MHz, CD3OD): δ 3.20 (m, 1H), 3.40 (m, 1H), 4.25 (t, 1H), 6.82 (dd, 1H), 7.43 (m, 5H), 7.57 (s, 1H), 7.60 (m, 2H), 8.10 (d, 2H), 8.75 (s, 1H).

後処理

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated to dryness
  4. dissolutionThe residue was dissolved in 2.5 ml of methanol
  5. customthe product was purified with Prep-LC

出典と根拠

ORDレコード
ord-af95ff8bef004d9c8df6fb0254d0949c
出典データセット
uspto-grants-2011_01
特許番号
US07875622B2

関連ノート

読み込み中…