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Sodium hydride → 1-((3-phenylbenzo[b]thiophen-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 243343
Notes
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Reaction equation

HRID 243343 reaction equation
[H-].[Na+].[NH:3]1[C:7]2=[N:8][CH:9]=[N:10][C:11]([NH2:12])=[C:6]2[CH:5]=[N:4]1.[C:13]1([C:19]2[C:20]3[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=3[S:22][C:23]=2[CH2:24]OS(C)(=O)=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[C:13]1([C:19]2[C:20]3[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=3[S:22][C:23]=2[CH2:24][N:3]2[C:7]3=[N:8][CH:9]=[N:10][C:11]([NH2:12])=[C:6]3[CH:5]=[N:4]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 86668872(3-Phenylbenzo[b]thiophen-2-yl)methyl methanesulfonate

Product 1

HCID 681584941-((3-phenylbenzo[b]thiophen-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (60% in mineral oil, 13 mg, 0.314 mmol) was added in one portion to a mixture of 1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (42 mg, 0.314 mmol) in DMF (5 mL) at RT. After 5 min stirring a solution of methanesulfonic acid 3-phenylbenzo[b]thiophen-2-ylmethyl ester from Example 26 (100 mg, 0.314 mmol) in DMF (1 mL) was added dropwise and stirring at RT was continued for 30 min. The reaction mixture was then quenched by addition of water and diluted with EtOAc. The aqueous phase was further extracted with EtOAc (2×100 mL) and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc) and triturated from MeOH with water affording 164 as an off-white solid (17 mg, 15%). LCMS: RT 4.13 min [M+H]+ 358.1. 1H NMR (DMSO, 400 MHz): δ 8.23 (1H, s), 8.16 (1H, s), 7.95-7.90 (1H, m), 7.70-7.59 (4H, m), 7.56-7.49 (2H, m), 7.42-7.35 (2H, m), 5.72 (2H, s)

Workup

  1. additionwas added dropwise
  2. customThe reaction mixture was then quenched by addition of water
  3. additiondiluted with EtOAc
  4. extractionThe aqueous phase was further extracted with EtOAc (2×100 mL)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc)
  9. customtriturated from MeOH with water affording 164 as an off-white solid (17 mg, 15%)

Sources & evidence

ORD record
ord-588fa2c250574823996d75a9d52cca27
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08653089B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes