Water → HCID 68109074, compound

HRID 1809711Notes

Reaction equation

HRID 1809711 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][C:13](Cl)=[N:14][CH:15]=3)[N:10]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:46]([O:50][C:51](=[O:60])[NH:52][CH:53]1[CH2:58][CH2:57][CH:56]([NH2:59])[CH2:55][CH2:54]1)([CH3:49])([CH3:48])[CH3:47].O>CN(C=O)C>[C:46]([O:50][C:51](=[O:60])[NH:52][CH:53]1[CH2:54][CH2:55][CH:56]([NH:59][C:13]2[N:12]=[C:11]3[N:10]([C:18]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:9]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=4)[C:16]3=[CH:15][N:14]=2)[CH2:57][CH2:58]1)([CH3:49])([CH3:47])[CH3:48]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 866679653-(3-bromo-phenyl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 68109074HCID 68109074, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-(3-bromo-phenyl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine (from Example 42 supra) (1.10 g, 2.0 mmol) in DMF (20 mL) was add DIPEA (0.39 g, 2.8 mmol) and (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (0.60 g, 2.8 mmol). This mixture was stirred at 120° C. for 12 hours. After cooling to room temperature, the reaction mixture was poured into water (100 mL) and the resulting precipitate was collected by filtration. The obtained yellow solid was purified by chromatography (silica gel, MeOH:dichloromethane, 1:100) to give a light solid which was washed with ether (4 mL) to give {4-[3-(3-bromo-phenyl)-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid. (Yield 730 mg, 50.1%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe obtained yellow solid was purified by chromatography (silica gel, MeOH:dichloromethane, 1:100)
  4. customto give a light solid which
  5. washwas washed with ether (4 mL)

Sources & evidence

ORD record
ord-5c3c630a88ac444186d488b5079ecd7d
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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