4-Methoxybenzylamine → HCID 86699674, compound

HRID 1487185Notes

Reaction equation

HRID 1487185 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([Cl:15])[N:3]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C>CN(C)C=O>[Cl:1][C:2]1[N:3]=[C:4]([Cl:15])[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([NH:23][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[N:7]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 27374117Ethyl (2,4,6-trichloropyrimidin-5-yl)acetate

Product 1

HCID 86699674HCID 86699674, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-(2,4,6-trichloropyrimidin-5-yl)acetate (43.3 g, 160.7 mmol) in N,N-dimethylformamide (500 mL) was added 4-Methoxybenzylamine (24.2 g, 176.8 mmol) and N,N′-diisopropylethylamine (24.9 g, 192.9 mmol), the reaction mixture was heated to 60° C. for 1 h. Quenched with water, extracted with ethyl acetate, and the organic extracts were combined, washed with hydrochloride (1 N), brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the as a pale-yellow solid (27.1 g, yield 45.6%). 1H NMR (400 MHz, CDCl3) δ ppm 7.29 (dd, J=6.0, 3.9 Hz, 1H), 6.93-6.85 (m, 1H), 6.14 (s, 1H), 4.63 (d, J=5.3 Hz, 2H), 4.15 (q, J=7.1 Hz, 2H), 3.83 (s, 3H), 3.62 (s, 2H), 1.23 (t, J=7.1 Hz, 2H).

Workup

  1. customQuenched with water
  2. extractionextracted with ethyl acetate
  3. washwashed with hydrochloride (1 N), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b7c2e47e5e014bb1bc5c82c67aecbeb7
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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