Sodium hydride → (4-Benzyloxy-3-methoxybenzyl)(5-chloro-2,6-dimethylpyrimidin-4-yl)amine

HRID 2415097Notes

Reaction equation

HRID 2415097 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][C:20]=1[O:27][CH3:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+]>CN1CCCC1=O>[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:1][C:2]2[C:7]([Cl:8])=[C:6]([CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=2)=[CH:21][C:20]=1[O:27][CH3:28])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2979621-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzeneHCID 5938434-Amino-5-chloro-2,6-dimethylpyrimidine

Product 1

HCID 22640039(4-Benzyloxy-3-methoxybenzyl)(5-chloro-2,6-dimethylpyrimidin-4-yl)amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In analogy to the method described in example A1, 3.67 g (22.8 mmol) of 4-amino-5-chloro-2,6-dimethylpyrimidine, 6.0 g (22.8 mmol) of 4-benzyloxy-3-methoxybenzyl chloride and 0.91 g (23 mmol) of sodium hydride (60% suspension in liquid paraffin) are reacted in a total of 190 ml of N-methylpyrrolidone. After chromatography on silica gel (mobile phase: toluene/dioxane=10:1) and crystallization from petroleum ether, the title compound is isolated as a pale beige solid. Yield: 3.42 g (39% of theory). m.p.: 101-105° C.

Workup

  1. customAfter chromatography on silica gel (mobile phase: toluene/dioxane=10:1) and crystallization from petroleum ether

Sources & evidence

ORD record
ord-fdcde48a9c0c43328d06be287cd508de
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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