Acetic Acid → 5-{4-[5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinic acid

HRID 2102373ノート

反応式

HRID 2102373 の反応式
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[C:16]3[C:23]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[CH:22][S:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:7]=[N:6][CH:5]=1.[OH-].[K+].C(O)(=O)C>CO>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C:23]2[C:16]3[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:8]4[CH:7]=[N:6][CH:5]=[C:4]([CH:9]=4)[C:3]([OH:31])=[O:2])=[N:20][CH:19]=[N:18][C:17]=3[S:21][CH:22]=2)=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 11647803Methyl 5-4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxynicotinate

生成物 1

HCID 116557445-{4-[5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinic acid収率 82,139.102%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of methyl-5-{4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinate (0.010 g, 0.023 mmol) and potassium hydroxide (0.0112 g, 0.200 mmol) in methanol (0.5 mL) was stirred at room temperature for 12 h. Acetic acid (200 mg, 3.33 mmol) was then added, and the reaction solvent was removed by evaporation. The product was purified by column chromatography over silica gel using 5% methanol in dichloromethane as eluant to afford 8 g (83%) 5-{4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinic acid hydroformate as white solid. MS [M+H]=424.1, LC/MS (EI) tR 3.89 min (Method D), 1H NMR (10% MeOD/CDCl3) δ (ppm) 8.94 (s, 1H), 8.73 (s, 1H), 8.28 (s, 1H), 7.68 (s, 1H), 7.40-7.30 (m, 3H), 7.10 (t, J=8.4 Hz, 2H), 3.84 (t, J=6.3 Hz, 2H), 2.68 (t, J=7.2 Hz, 2H), 1.75-1.59 (m, 2H), 1.59-1.45 (m, 2H)

後処理

  1. customthe reaction solvent was removed by evaporation
  2. customThe product was purified by column chromatography over silica gel using 5% methanol in dichloromethane as eluant

出典と根拠

ORDレコード
ord-f689128c9b134d8eb33e3ea3cbf8a08c
出典データセット
uspto-grants-2009_08
特許番号
US07576080B2

反応ノート

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