4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-pyridiniumolate → 3-(4-phenoxyphenyl)-1-(4-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 2056161노트

반응식

HRID 2056161 반응식
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C:24]3[CH:29]=[CH:28][N+:27]([O-])=[CH:26][CH:25]=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)[C:3]=12.O.[PH2]([O-])=O.[Na+]>[Pd].C(O)(=O)C>[O:17]([C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[N:7][C:2]=3[NH2:1])[N:8]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[N:9]=2)=[CH:16][CH:15]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 2

HCID 223472784-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-pyridiniumolateHCID 178418950HCID 178418950, 화합물2회

생성물 1

HCID 223472473-(4-phenoxyphenyl)-1-(4-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine수율 20%

시약·촉매·용매 2

HCID 23938Palladium촉매3회HCID 176Acetic Acid용매

실험 절차

A suspension of 4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-pyridiniumolate (0.100 g, 0.00025 mol) and 10% palladium on carbon (0.016 g, 0.00002 mol) in acetic acid (3 mL) was reacted with sodium hypophosphite monohydrate (0.033 g, 0.00038 mol) at 60° C. After 2 hours, an additional 10% palladium on carbon (0.016 g, 0.00002 mol) was added. The mixture was stirred 18 hours after which time additional 10% palladium on carbon (0.016 g, 0.00002 mol) and sodium hypophosphite monohydrate (0.033 g, 0.00038 mol) was added. The mixture was stirred for an additional 24 hours. The mixture was filtered through Celite® 521, washing with acetic acid. The solvent was removed in vacuo, and the residue was purified by preparative RP-HPLC (Rainin C18, 8 mm, 300 Å, 25 cm; 40% isocratic for five minutes, then 40%-100% acetonitrile—0.1M ammonium acetate over 30 min, 21 mL/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to give 3-(4-phenoxyphenyl)-1-(4-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.020 g, 0.00005 mol) as a white solid:

후처리

  1. additionwas added
  2. filtrationThe mixture was filtered through Celite® 521
  3. washwashing with acetic acid
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by preparative RP-HPLC (Rainin C18, 8 mm, 300 Å, 25 cm
  6. wait40% isocratic for five minutes
  7. wait40%-100% acetonitrile—0.1M ammonium acetate over 30 min
  8. customThe acetonitrile was removed in vacuo

출처 및 근거

ORD 기록
ord-e6a4dab063ba442da0fc71b130384bab
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07332497B2

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