Ethyl Acetate → Methyl 2-amino-4-(4-fluorophenyl)-6-isopropylpyrimidine-5-carboxylate

HRID 50104Notes

Reaction equation

HRID 50104 reaction equation
[NH2:1][C:2](=[C:10]([C:15](=O)[CH:16]([CH3:18])[CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[N:20]#[C:21][NH2:22].C(OCC)(=O)C>O>[NH2:22][C:21]1[N:1]=[C:2]([C:3]2[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=2)[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:15]([CH:16]([CH3:18])[CH3:17])[N:20]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 9864CyanamideHCID 178500902HCID 178500902, compound

Product 1

HCID 10424248Methyl 2-amino-4-(4-fluorophenyl)-6-isopropylpyrimidine-5-carboxylateYield 8.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 1.33 g of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate (5.00 mmol) in 4.20 g of 50% strength aqueous cyanamide solution (50.0 mmol) was heated to reflux. After 17 h, it was cooled to room temperature and treated with ethyl acetate (5 ml) and water (5 ml). The undissolved solid was filtered off. The organic phase was separated off and the aqueous phase was extracted with ethyl acetate (2×5 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo. The crude product (0.97 g) was purified by flash chromatography on silica gel (eluent: methylene chloride). 121.6 mg of methyl 2-amino-4-(4-fluorophenyl)-6-isopropylpyrimidine-5-carboxylate were obtained in the form of a colourless solid.

Workup

  1. temperaturewas heated to reflux
  2. filtrationThe undissolved solid was filtered off
  3. customThe organic phase was separated off
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×5 ml)
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe crude product (0.97 g) was purified by flash chromatography on silica gel (eluent: methylene chloride)

Sources & evidence

ORD record
ord-bb7487b9d98e49fba13400d711c217b0
Source dataset
uspto-grants-2004_03
Patent number
US06710178B2

Reaction notes

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