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Potassium Carbonate → 1-(4-(6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea

HRID 347457
Notes
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Reaction equation

HRID 347457 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13](=[O:22])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[S:11])[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:24]1[N:29]=[C:28]([Cl:30])[N:27]=[C:26]2[N:31]([CH3:34])[N:32]=[CH:33][C:25]=12.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:30][C:28]1[N:27]=[C:26]2[N:31]([CH3:34])[N:32]=[CH:33][C:25]2=[C:24]([O:8][C:7]2[CH:6]=[CH:5][C:4]([NH:9][C:10]([NH:12][C:13](=[O:22])[CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)=[S:11])=[CH:3][C:2]=2[F:1])[N:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2222474,6-dichloro-1-methyl-1H-pyrazolo(3,4-d)pyrimidineHCID 210814951-(3-Fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea

Product 1

HCID 117058221-(4-(6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)thioureaYield 60%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a mixture of 1-(3-fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea (24 mg, 0.075 mmol), 4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (15.3 mg, 0.075 mmol, preparation: J. Org. Chem. 1958, 23, 852, the disclosure of which is herein incorporated by reference) and K2CO3 (10 mg, 0.075 mmol) was added DMF (2 mL). The reaction was stirred at RT for 24 h. The reaction was quenched with water (2 mL) and CH2Cl2 (5 mL). The organic layer was separated, dried with sodium sulfate, concentrated in vacuo and purified by reverse phase preparative HPLC to give the title compound (22.9 mg, 60%) as a white solid. MS(ESI+) m/z 457 (M+H)+.

Workup

  1. custom15.3 mg, 0.075 mmol, preparation
  2. customThe reaction was quenched with water (2 mL) and CH2Cl2 (5 mL)
  3. customThe organic layer was separated
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-c82b04990c9f4ed79cde143869b80c2a
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07173031B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes