Diisopropylethylamine → HCID 58504396, compound

HRID 2367564Notes

Reaction equation

HRID 2367564 reaction equation
[CH2:1]([C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][NH:4]1)[CH3:2].CCN(C(C)C)C(C)C.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[C:21]([NH:26][CH3:27])[N:20]=1>CC#N>[Cl:18][C:19]1[CH:24]=[C:23]([N:4]2[CH2:5][CH2:6][O:7][CH2:8][C@H:3]2[CH2:1][CH3:2])[N:22]=[C:21]([NH:26][CH3:27])[N:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2598804,6-Dichloro-n-methylpyrimidin-2-amineHCID 14267783(3R)-3-Ethylmorpholine

Product 1

HCID 58504396HCID 58504396, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

(3R)-3-Ethylmorpholine (5 g, 43.4 mmol) was taken up in CH3CN (100 mL) and Hunig's base (15.2 mL, 87 mmol), followed by the addition of 4,6-dichloro-N-methyl-2-pyrimidinamine (6.96 g, 39.1 mmol), and the reaction was heated to 130° C. overnight in a sealed tube. The reaction mixture was concentrated and then purified via flash chromatography (0-15% EtOAc/CHCl3, 400 g). Fractions were combined and concentrated to afford the title compound (1.6 g) as a colorless oil. LC-MS (ES) m/z=257 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified via flash chromatography (0-15% EtOAc/CHCl3, 400 g)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-296545791e0e455f90a5e6485e13975e
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…