2-(Dimethylamino)ethanol → HCID 68288048, compound

HRID 1396907Notes

Reaction equation

HRID 1396907 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[O-]CC.[Na+].[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][OH:17]>CN(C)C=O>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][O:17][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 3457522-Chloro-4-aminopyrimidineHCID 2723922Sodium ethoxide

Product 1

HCID 68288048HCID 68288048, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-chloro-4-pyrimidinamine (300 mg, 2.316 mmol), sodium ethoxide (189 mg, 2.78 mmol) and 2-(dimethylamino)ethanol (349 μl, 3.47 mmol) in N,N-dimethylformamide (DMF) (2.9 mL) was heated to 180° C. via a microwave reactor for min. The reaction was purified by RP-HPLC to yield 2-{[2-(dimethylamino)ethyl]oxy}-4-pyrimidinamine (111 mg, 0.609 mmol, 26% yield). MS (ES+) m/z 183.0 (MH+).

Workup

  1. customThe reaction was purified by RP-HPLC

Sources & evidence

ORD record
ord-d1b8c4e7d21143c692326159fcf4b673
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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