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 1693515노트

반응식

HRID 1693515 반응식
[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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3da1820876ff43cc9f6ca99d1e3e23ce
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158634B2

반응 노트

불러오는 중…