Water → HCID 17848301, compound

HRID 917583Notes

Reaction equation

HRID 917583 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Cl[C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([Cl:23])[CH:16]=2)[C:10]([C:24]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=2)=[O:25])=[CH:9][N:8]=1.O>CN(C)C=O>[CH3:1][N:2]([C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([Cl:23])[CH:16]=2)[C:10]([C:24]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=2)=[O:25])=[CH:9][N:8]=1)[CH2:3][CH2:4][OH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 80162-(Methylamino)ethanolHCID 17848364HCID 17848364, compound

Product 1

HCID 17848301HCID 17848301, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-methylaminoethanol 100 mg in dimethylformamide 1 ml is added at room temperature to a solution of 2-chloro-5-(3,4,5-trimethoxyphenylcarbonyl)-4-(3-chloro-4-methoxybenzylamino) pyrimidine (120 mg) prepared in above Example 1-(3) in dimethylformamide (1 ml). The mixture is stirred at room temperature for 1 hour and thereto is added water 50 ml. The mixture is extracted with ethyl acetate-chloroform and the extract is subjected to silica gel chromatography (solvent:chloroform-methanol 5%) to give 2-(N-methyl-N-(2-hydroxyethyl)amino)-5-(3,4,5-trimethoxyphenylcarbonyl)-4-(3-chloro-4-methoxybenzylamino)pyrimidine 110 mg as white crystals. mp 166.5-168° C.

Workup

  1. extractionThe mixture is extracted with ethyl acetate-chloroform

Sources & evidence

ORD record
ord-2bd93c47748147f48a27637e8aa081dc
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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