Triethylamine → 2-((2,6-Dichloropyrimidin-4-yl)(methyl)amino)propan-1-ol

HRID 2171323Notes

Reaction equation

HRID 2171323 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[CH3:17][NH:18][CH:19]([CH3:22])[CH2:20][OH:21]>C(#N)C.CN(C)C=O>[Cl:1][C:2]1[N:3]=[C:4]([N:18]([CH3:17])[CH:19]([CH3:22])[CH2:20][OH:21])[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 773782,4,6-TrichloropyrimidineHCID 126957852-(Methylamino)propan-1-ol

Product 1

HCID 867283112-((2,6-Dichloropyrimidin-4-yl)(methyl)amino)propan-1-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2,4,6-trichloropyrimidine (5.0 g, 27 mmol) and triethylamine (11 mL, 82 mmol) in acetonitrile (20 mL) was slowly added a solution of 2-(methylamino)propan-1-ol (2.9 g, 33 mmol) in N,N-dimethylformamide (DMF) (2 mL) at 0° C. The reaction mixture was stirred at same temperature for 1 h, then filtered through a thin pad of celite and concentrated. Purification via silica gel flash chromatography (petroleum ether/ethyl acetate=4/1˜1/1) afforded the title product as an oil.

Workup

  1. filtrationfiltered through a thin pad of celite
  2. concentrationconcentrated
  3. customPurification via silica gel flash chromatography (petroleum ether/ethyl acetate=4/1˜1/1)

Sources & evidence

ORD record
ord-c2452bc4e4bb4aafa11ffe1d1013cb26
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

Loading…