Ammonium formate → 3-(4-phenoxyphenyl)-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 432132노트

반응식

HRID 432132 반응식
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([NH2:23])=[C:17]3[C:16]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:26][CH:25]=3)=[N:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[O:30]([C:27]1[CH:26]=[CH:25][C:24]([C:16]2[C:17]3[C:18](=[N:19][CH:20]=[N:21][C:22]=3[NH2:23])[N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:15]=2)=[CH:29][CH:28]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 98262731-(1-benzyl-4-piperidinyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine2회

생성물 1

HCID 223472623-(4-phenoxyphenyl)-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine수율 77.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

1-(1-benzyl-4-piperidinyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Compound 1) (1.224 g, 2.57 mmol), 10% Palladium on carbon (1.22 g) and ammonium formate(0.81 g, 12.84 mmol) were mixed with 21 ml of methanol. After stirring at room temperature for 6 hours, the reaction mixture was filtered and washed with hot methanol. Solvent was removed and the residue was taking into dichloromethane and the organic layer was washed, dried, and evaporated to give 0.77 g of 3-(4-phenoxyphenyl)-1-(4-piperidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. 1H NMR (CDCl3) 2.05 (d, J=12.17 Hz, 2H), 2.26 (m, 2H), 2.87 (m, 2H), 3.29 (d, J=12.76 Hz), 4.89 (m, 1H), 5.54 (s, 2H), 7.09 (m, 2H), 7.15 (m, 3H), 7.39 (m, 2H), 7.67 (d, J=9.39 Hz, 2H), 8.37 (s, 1H); LC/MS (MH+32 387).

후처리

  1. filtrationthe reaction mixture was filtered
  2. washwashed with hot methanol
  3. customSolvent was removed
  4. washthe organic layer was washed
  5. customdried
  6. customevaporated

출처 및 근거

ORD 기록
ord-9f31e207fe064fef932b1499c78d99ed
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

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