Water → HCID 56644956, compound

HRID 570745Notes

Reaction equation

HRID 570745 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]([F:13])([F:12])[F:11])[N:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:16][CH:15]=2)[C:4](=[O:26])[CH:3]=1.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29].O>CN(C)C(=O)C>[F:24][C:22]([F:25])([F:23])[CH2:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([N:5]2[C:4](=[O:26])[C:3]3[CH2:29][CH2:28][C:27](=[O:30])[NH:1][C:2]=3[N:7]=[C:6]2[CH2:8][CH2:9][C:10]([F:13])([F:11])[F:12])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13140Acryloyl chlorideHCID 86685400HCID 86685400, compound

Product 1

HCID 56644956HCID 56644956, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 6-amino-3-(4-(2,2,2-trifluoroethoxy)phenyl)-2-(3,3,3-trifluoropropyl)pyrimidin-4(3H)-one (1.0 g) in N,N-dimethylacetamide (30 mL) was heated to 60° C., acryloyl chloride (0.85 mL) was added thereto, and the mixture was stirred for 10 min. To the reaction mixture was added water under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), diolpropylsilane-bonded silica gel column chromatography (ethyl acetate/hexane) and then silica gel column chromatography (ethyl acetate/hexane). The obtained solid was recrystallized from ethyl acetate-hexane to give the title compound (0.72 g) as a solid. The solid (487 mg) was recrystallized from ethyl acetate to give the title compound (300 mg) as a solid.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane), diolpropylsilane-bonded silica gel column chromatography (ethyl acetate/hexane)
  6. customThe obtained solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a98b89fd7c1942b5bbf9d39374669ca8
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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