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

HRID 1890461Notes

Reaction equation

HRID 1890461 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 20.3%

Procedure

The product is prepared according to the procedure described in Stage 1 of Example 2, using 550 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 2-aminophenol. After purification by silica gel column chromatography, elution being carried out with pure CH2Cl2 then CH2Cl2/MeOH: 95/05, 149 mg of N-(4-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide obtained in the form of a grey solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter purification
  3. washby silica gel column chromatography, elution

Sources & evidence

ORD record
ord-3082d2d23228427dbfabcbad7eee8f5c
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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