2-Amino-5-fluorophenol → N-(4-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydro-pyrimidin-2-yl]acetamide

HRID 880105Notes

Reaction equation

HRID 880105 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15]([O-:17])=O)[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na+].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[OH:27]>>[F:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:15](=[O:17])[CH2:14][C:9]2[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[N:8]=2)=[C:21]([OH:27])[CH:22]=1

Participants

3

Reactant 2

HCID 1857632-Amino-5-fluorophenolHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136332410N-(4-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydro-pyrimidin-2-yl]acetamideYield 22.3%

Procedure

The product is prepared according to the procedure described in Example 5, using 500 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate and 815 mg of 2-amino-5-fluorophenol in place of the 2,4-difluoroaniline. After purification by silica column chromatography, eluent: CH2Cl2/MeOH 955, 149 mg of N-(4-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the form of a grey solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter purification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-d90d520993a147cfb56460dc9cb7a533
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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