Dichloromethane → 2-((4-amino-3-(3-hydroxypropyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one

HRID 239655Notes

Reaction equation

HRID 239655 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:15][C:16]3[O:17][C:18]4[C:23]([C:24](=[O:32])[C:25]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:9]=[C:10]([C:11]#[C:12][CH2:13][OH:14])[C:3]=12.ClCCl>CO.[Pd]>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:15][C:16]3[O:17][C:18]4[C:23]([C:24](=[O:32])[C:25]=3[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:9]=[C:10]([CH2:11][CH2:12][CH2:13][OH:14])[C:3]=12

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 582691602-((4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one

Product 1

HCID 582691562-((4-amino-3-(3-hydroxypropyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-oneYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of example 59 (0.170 g, 0.401 mmoles) in methanol (4 ml), palladium on charcoal 1 (10%, 0.050 g) was added and hydrogenated at 5 kg/cm2 for 48 h. The reaction mixture filtered through celite pad and washed with methanol. The filtrate was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as brown solid (0.072 g, 42% yield). MP: 182-184° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.11(s,1H), 8.05(dd, J=8.0, 1.6 Hz, 1H), 7.76(m,1H), 7.49(t, J=7.1 Hz, 1H), 7.39-7.20(m, 8H), 4.62(t, J=4.6 Hz, 1H),3.45(q, J=6.1 Hz, 2H), 2.92(t, J=7.4 Hz, 2H), 1.78(m,2H). Mass: 427.87(M+).

Workup

  1. filtrationThe reaction mixture filtered through celite pad
  2. washwashed with methanol
  3. dry with materialThe filtrate was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-1f95a12a5b404bca88369b7516172e6d
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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