Potassium Carbonate → 2-((4-Amino-3-(3-fluoro-4-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-5-bromo-3-(2-chlorobenzyl)quinazolin-4(3H)-one

HRID 400547Notes

Reaction equation

HRID 400547 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:22])[N:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[C:6]([CH2:12]Cl)=[N:7]2.C(=O)([O-])[O-].[K+].[K+].[NH2:29][C:30]1[N:35]=[CH:34][N:33]=[C:32]2[NH:36][N:37]=[C:38]([C:39]3[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([F:46])[CH:40]=3)[C:31]=12>CN(C=O)C>[NH2:29][C:30]1[N:35]=[CH:34][N:33]=[C:32]2[N:36]([CH2:12][C:6]3[N:5]([CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:4](=[O:22])[C:3]4[C:8](=[CH:9][CH:10]=[CH:11][C:2]=4[Br:1])[N:7]=3)[N:37]=[C:38]([C:39]3[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([F:46])[CH:40]=3)[C:31]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 665792385-bromo-3-(2-chlorobenzyl)-2-(chloromethyl)quinazolin-4(3H)-oneHCID 178508721HCID 178508721, compound

Product 1

HCID 1363502752-((4-Amino-3-(3-fluoro-4-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-5-bromo-3-(2-chlorobenzyl)quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of compound (8) (200 mg, 0.502 mmol) and potassium carbonate (83 mg, 0.60 mmol) in DMF (2.0 mL) was added a solution of 4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluorophenol (see Table 1, below) (148 mg, 0.602 mmol) in DMF (2.0 mL) and the reaction mixture stirred at RT for 18 hr. The solvent was removed in vacuo and the crude material was purified by flash column chromatography, eluting with 5% methanol in DCM, to afford the title compound, Intermediate D (81 mg, 27%) as a off-white solid: m/z 606/608 (M+H)+ (ES+) (Method B).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude material was purified by flash column chromatography
  3. washeluting with 5% methanol in DCM

Sources & evidence

ORD record
ord-380f5e6d4e9c4f7eb6079eb08efccffb
Source dataset
uspto-grants-2014_06
Patent number
US08741909B2

Reaction notes

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