Guanidine Hydrochloride → 6-[4-(2-Amino-pyrimidin-4-yl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693515ノート

反応式

HRID 1693515 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([C:30](=O)[CH:31]=[CH:32]N(C)C)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.Cl.[NH2:38][C:39]([NH2:41])=[NH:40].[OH-].[Na+].[NH4+].[Cl-]>CO>[NH2:40][C:39]1[N:41]=[C:30]([C:27]2[CH:26]=[CH:25][C:24]([C:9]3[N:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[C:13](=[O:14])[C:12]4[CH:15]=[N:16][N:17]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[C:11]=4[N:10]=3)=[CH:29][CH:28]=2)[CH:31]=[CH:32][N:38]=1

参加物

6

反応物 4

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 672827725-(4-Chloro-phenyl)-6-[4-(3-dimethylamino-acryloyl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

生成物 1

HCID 578980476-[4-(2-Amino-pyrimidin-4-yl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A suspension of 5-(4-chloro-phenyl)-6-[4-(3-dimethylamino-acryloyl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (24 mg, 0.048 mmol) in MeOH (1 mL) is treated with guanidine hydrochloride (12 mg, 0.13 mmol) and NaOH (4 mg, 0.1 mmol) at 80° C. for 34 h. After cooling down to room temperature, the mixture is treated with saturated aqueus NH4Cl solution (2 mL) and extracted with EtOAc (3×2 mL). The organic layers are concentrated and purified by preparative thin layer chromatography (silica gel, 2.5% MeOH/CH2Cl2) to provide the titled compound 6-[4-(2-amino-pyrimidin-4-yl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as a white solid. 1H NMR (CDCl3) δ(ppm) 8.35(b, 1H), 8.34(s, 1H), 8.14 (d, 2H), 7.92 (d, 2H), 7.51 (t, 2H), 7.46 (d, 2H), 7.35(t, 1H), 7.32(d, 2H), 7.12(d, 2H), 7.03(d, 1H), 5.34(b, 2H); HPLC-MS calculated for C27H18ClN7O (M+H+): 492.1. Found: 492.2.

後処理

  1. extractionextracted with EtOAc (3×2 mL)
  2. concentrationThe organic layers are concentrated
  3. custompurified by preparative thin layer chromatography (silica gel, 2.5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-3da1820876ff43cc9f6ca99d1e3e23ce
出典データセット
uspto-grants-2012_04
特許番号
US08158634B2

反応ノート

読み込み中…