Methylamine → N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-3-[2-(methylamino)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 550468Notes

Reaction equation

HRID 550468 reaction equation
[CH3:1][NH2:2].Cl[CH2:4][CH2:5][O:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[N:13][C:14]=2[NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)=[C:19]([Cl:32])[CH:18]=2)[NH:9][N:8]=1>O.C(O)C>[Cl:32][C:19]1[CH:18]=[C:17]([NH:16][C:14]2[N:13]=[CH:12][N:11]=[C:10]3[NH:9][N:8]=[C:7]([O:6][CH2:5][CH2:4][NH:2][CH3:1])[C:15]=23)[CH:22]=[CH:21][C:20]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 117050313-(2-chloroethoxy)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 11611980N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-3-[2-(methylamino)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 14%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Methylamine in water (40% solution, 2 ml) was added to a suspension of 3-(2-chloroethoxy)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine (prepared as described in Example 12/0.4 g, 0.89 mmol) in ethanol (4 ml) and the reaction mixture was heated at 120° C. for 5 minutes in a microwave reactor. The resulting solution was concentrated in vacuo and the residue purified by chromatography using DCM to DCM-10% methanol/7N ammonia as eluant to give the title compound as a white solid (57 mg, 14%); Mass Spectrum: 443.3 (MH+/retention time 1.5 minutes).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-1b385b2c14e34f34a397905300ffaf7f
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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