Dichloromethane → HCID 59627819, compound

HRID 1907839Notes

Reaction equation

HRID 1907839 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[N:12]1[C:21]2[C:16](=[CH:17][C:18]([CH2:22][NH2:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C.ClCCl>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:23][CH2:22][C:18]2[CH:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[N:12]=[CH:13][CH:14]=[CH:15]3)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 15143846-(Aminomethyl)quinoline

Product 1

HCID 59627819HCID 59627819, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2,4-dichloro-5-nitro-pyrimidine (2.80 g, 14.4 mmol) in dioxane (20 mL) was added dropwise a solution of quinolin-6-ylmethanamine (2.28 g, 14.4 mmol) in dioxane (4 mL) and DIPEA (2.56 mL, 14.7 mmol). The reaction mixture was stirred at room temperature for 2 hours. Dichloromethane (20 mL) was then added to the reaction mixture. The solvent was removed in vacuo and the crude product was purified by flash chromatography over silica gel, using 50% EtOAc-hexane, gave the desired product (3.18 g, 70%) as a pale yellow solid. LCMS (APCI) m/z 316.0 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-75db5827af524ca9a3b1fd9da4d74953
Source dataset
uspto-grants-2013_12
Patent number
US08598184B2

Reaction notes

Loading…