Chlorotrimethylsilane → 4-(cyclopropylamino)-2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

HRID 2381720Notes

Reaction equation

HRID 2381720 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:23][CH:24]2[CH2:26][CH2:25]2)[C:5]2[C:10]([C:11]#[N:12])=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[NH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[CH2:32][CH2:31]2.C[Si](Cl)(C)C>C(O)CCC>[CH:24]1([NH:23][C:4]2[C:5]3[C:10]([C:11]#[N:12])=[CH:9][NH:8][C:6]=3[N:7]=[C:2]([NH:27][C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[NH:34][C:33](=[O:38])[CH2:32][CH2:31]4)[N:3]=2)[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 579903512-chloro-4-(cyclopropylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Product 1

HCID 579903684-(cyclopropylamino)-2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrileYield 37.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-chloro-4-(cyclopropylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (145 mg, 0.374 mmol), 6-amino-3,4-dihydroquinolin-2(1H)-one (60 mg, 0.370 mmol) and trimethylsilyl chloride (0.200 mL, 1.58 mmol) in nBuOH (4 mL) was stirred at 135° C. for 20 h. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (50 mg). MS 360.3 (M+H); UV 202.2, 292.7 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-3c111b442bac4d85a2a520de8cda1f0c
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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