Phenethylamine → HCID 1484521, compound

HRID 2367218Notes

Reaction equation

HRID 2367218 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[C:10]1([CH2:16][CH2:17][NH2:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CO>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:18][CH2:17][CH2:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 1484521HCID 1484521, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4,6-dichloro-2-pyrimidinamine (815 mg, 5.0 mmol), (2-phenylethyl)amine (665 mg, 5.5 mmol) and triethylamine (1.0 g, 10 mmol) in CH3OH (20 mL) was stirred at 60° C. for 2 hours. The reaction mixture was concentrated, and the resulting residue was subjected to flash chromatography on SiO2 (eluent: 1/1 EtOAc/petroleum ether) to afford the title compound (1.0 g, 81%) as light yellow solid. LC-MS (ES) m/z=249 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-02fc2b8b0bfc4164a67aa701464c0d3c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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