4-Aminopyridine → 2-(biphenyl-4-ylmethyl)-7-isobutyl-5-methyl-3-(pyridin-4-ylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81413

반응식

HRID 81413 반응식
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16](I)=[C:15]3[C:10]([N:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12](=[O:20])[N:13]([CH3:19])[C:14]3=[O:18])=[N:9]2)=[CH:3][CH:2]=1.[N:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(O[K])(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]([NH:37][C:34]3[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=3)=[C:15]3[C:10]([N:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12](=[O:20])[N:13]([CH3:19])[C:14]3=[O:18])=[N:9]2)=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 17274-AminopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 685050642-(biphenyl-4-ylmethyl)-3-iodo-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneHCID 178418922HCID 178418922, 화합물

생성물 1

HCID 426408852-(biphenyl-4-ylmethyl)-7-isobutyl-5-methyl-3-(pyridin-4-ylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
150 °C

실험 절차

2-(biphenyl-4-ylmethyl)-3-iodo-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (13.6 mg, 0.026 mmol) is dissolved in anhydrous and degassed THF, and then 4-pyridyl amine (13 mg, 0.132 mmol), Pd2(dba)3 (12 mg, 0.013 mmol) and Xantphos (9 mg, 0.016 mmol) are added, followed by tBuOK (7.5 mg, 0.065 mmol). The reaction mixture is heated in microwave at 150° C. for 40 minutes. After cooling and filtration, the filtrate is purified by a semi-preparative HPLC to give product. MS (ESI) m/z 481.2 [M+H]+

후처리

  1. customdegassed THF
  2. temperatureAfter cooling
  3. filtrationfiltration
  4. customthe filtrate is purified by a semi-preparative HPLC
  5. customto give product

출처 및 근거

ORD 기록
ord-5074a99527b24e97a904d6d5ca7f3a40
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846693B2

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