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Chlorotrimethylsilane → 6-(4-(cyclopropylamino)-5-(pyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-3,4-dihydroquinolin-2(1H)-one

HRID 2381647
Notes
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Reaction equation

HRID 2381647 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:27][CH:28]2[CH2:30][CH2:29]2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[NH2:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[NH:38][C:37](=[O:42])[CH2:36][CH2:35]2.C[Si](Cl)(C)C>C(O)CCC>[CH:28]1([NH:27][C:4]2[C:5]3[C:10]([C:11]4[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=4)=[CH:9][NH:8][C:6]=3[N:7]=[C:2]([NH:31][C:32]3[CH:33]=[C:34]4[C:39](=[CH:40][CH:41]=3)[NH:38][C:37](=[O:42])[CH2:36][CH2:35]4)[N:3]=2)[CH2:30][CH2:29]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6397Chlorotrimethylsilane2×HCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 579903022-chloro-N-cyclopropyl-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 579904176-(4-(cyclopropylamino)-5-(pyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-3,4-dihydroquinolin-2(1H)-oneYield 6.4%

Reagents, catalysts & solvents 1

HCID 263
1-Butanol
Solvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-chloro-N-cyclopropyl-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (85 mg, 0.19 mmol), 6-amino-3,4-dihydroquinolin-2(1H)-one (70 mg, 0.43 mmol) and TMSCl (0.100 mL, 0.79 mmol) in nBuOH (3 mL) was stirred at 135° C. for 18 h. More TMSCl (0.200 mL) was added. Stirring was continued at 135° C. for another 68 h. It was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (5 mg). MS 412.3 (M+H); UV 201.8, 295.8 nm.

Workup

  1. stirringStirring
  2. waitwas continued at 135° C. for another 68 h
  3. concentrationIt was then concentrated in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-cf1d3920412442788e6e8ef509805686
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258144B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes