2-(Bromomethyl)pyrimidine → 3-(Pyrimidin-2-yl)-2,2-bis(3-(trifluoromethoxy)phenyl)propanoic acid

HRID 1712756ノート

反応式

HRID 1712756 の反応式
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:5]=[C:6]([CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)[C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1.[Li]CCCC.Br[CH2:33][C:34]1[N:39]=[CH:38][CH:37]=[CH:36][N:35]=1>C1COCC1>[N:35]1[CH:36]=[CH:37][CH:38]=[N:39][C:34]=1[CH2:33][C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=1)([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:25])([F:26])[F:1])[CH:5]=1)[C:11]([OH:13])=[O:12]

参加物

5

反応物 3

HCID 220327572-(Bromomethyl)pyrimidineHCID 594583592,2-Bis(3-(trifluoromethoxy)phenyl)acetic acidHCID 178418339Butyllithium

生成物 1

HCID 594590353-(Pyrimidin-2-yl)-2,2-bis(3-(trifluoromethoxy)phenyl)propanoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

At −15° C. to a solution of 2,2-bis(3-(trifluoromethoxy)phenyl)acetic acid prepared as described in Procedure 73 (607 mg, 1.6 mmol) in THF (6 mL) was added nBuLi (1.6 mL, 2M in hexane, 3.2 mmol). The mixture was stirred at −15° C. for 45 min. 2-(Bromomethyl)pyrimidine (412 mg, crude) in THF (1 mL) was added and the reaction mixture was allowed to warm to rt and stirred for 18 h, then quenched with saturated NH4Cl. The aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layer was dried over MgSO4, filtered and concentrated to give 3-(pyrimidin-2-yl)-2,2-bis(3-(trifluoromethoxy)phenyl)propanoic acid as a yellow solid (437 mg, 58% crude). This crude solid was carried onto the next step without further purification.

後処理

  1. temperatureto warm to rt
  2. stirringstirred for 18 h
  3. customquenched with saturated NH4Cl
  4. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-67f87670b74d48378fd9b19f874f2725
出典データセット
uspto-grants-2010_09
特許番号
US07790770B2

反応ノート

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