Pyrrolidine → N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-3-(2-pyrrolidin-1-ylethoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 550469Notes

Reaction equation

HRID 550469 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:7][CH2:8][O:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[N:16][C:17]=2[NH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)=[C:22]([Cl:35])[CH:21]=2)[NH:12][N:11]=1>C(O)C>[Cl:35][C:22]1[CH:21]=[C:20]([NH:19][C:17]2[N:16]=[CH:15][N:14]=[C:13]3[NH:12][N:11]=[C:10]([O:9][CH2:8][CH2:7][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[C:18]=23)[CH:25]=[CH:24][C:23]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 117050313-(2-chloroethoxy)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 11591148N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-3-(2-pyrrolidin-1-ylethoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

Pyrrolidine (0.5 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 12/0.2 g, 0.44 mmol) in ethanol (2 ml) and the reaction mixture was heated at 120° C. for 10 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 beige solid (67 mg, 31%); Mass Spectrum: 483.3 (MH+/retention time 1.56 minutes).

Workup

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

Sources & evidence

ORD record
ord-1d2991627b6b495d85602b78bbda1560
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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