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

HRID 2281499Notes

Reaction equation

HRID 2281499 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]3[C:25]([C:26]#[N:27])=[CH:24][NH:23][C:7]=3[N:8]=[C:9]([NH:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17](=[O:22])[CH2:16][CH2:15]4)[N:10]=2)[CH2:3][CH2:2]1.C([O-])([O-])=[O:29].[K+].[K+].OO>CS(C)=O>[CH:1]1([NH:4][C:5]2[C:6]3[C:25]([C:26]([NH2:27])=[O:29])=[CH:24][NH:23][C:7]=3[N:8]=[C:9]([NH:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17](=[O:22])[CH2:16][CH2:15]4)[N:10]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 579903684-(cyclopropylamino)-2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Product 1

HCID 579904244-(cyclopropylamino)-2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamideYield 22.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-(cyclopropylamino)-2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (30 mg, 0.083 mmol), K2CO3 (100 mg, 0.724 mmol) and H2O2 (50% aq., 0.500 mL) in DMSO (1 mL) was heated at 100° C. for 5 min. Gas evolved violently. After cooling down, the mixture was purified by HPLC to give the titled compound (7 mg). MS 378.4 (M+H); UV 200.4, 241.8, 295.8 nm.

Workup

  1. temperatureAfter cooling down
  2. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-5c1e920fa9a44307888e635a014ac885
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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