Ethyl cyanoacetate → 6-Amino-2-(2-propoxyphenyl)pyrimidin-4[3H]-one

HRID 892430Notes

Reaction equation

HRID 892430 reaction equation
[C:1]([CH2:3][C:4](OCC)=[O:5])#[N:2].[CH2:9]([O:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH2:17])=[NH:16])[CH2:10][CH3:11]>C(O)C.O>[NH2:2][C:1]1[N:17]=[C:15]([C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12][CH2:9][CH2:10][CH3:11])[NH:16][C:4](=[O:5])[CH:3]=1

Participants

5

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 41969722-Propoxybenzimidamide

Product 1

HCID 1355065006-Amino-2-(2-propoxyphenyl)pyrimidin-4[3H]-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl cyanoacetate (4.52 g) was added to a stirred solution of 2-propoxybenzamidine in ethanol (prepared from sodium, 1.84 g., in ethanol, 100 ml, and 2-propoxybenzamidine methanesulphonate, 11.61 g). The reaction mixture was stirred at ambient temperature for 18 hours and then evaporated under reduced pressure to leave a residue which was dissolved in water. The aqueous solution was extracted with diethyl ether (2×25 ml) and the combined ether extracts were washed with water. The combined aqueous phase was treated with glacial acetic acid to pH 5 to precipitate a crude product. Further crude product was obtained by extracting the ether extracts with 1 normal sodium hydroxide (2×30 ml) and acidifying the combined alkaline extracts with glacial acetic acid to pH 5. The combined crude product was recrystallised from isopropanol to yield the title compound, 2.34 g, m.p. 183.5°-184.5° C.

Workup

  1. customevaporated under reduced pressure
  2. customto leave a residue which
  3. extractionThe aqueous solution was extracted with diethyl ether (2×25 ml)
  4. washthe combined ether extracts were washed with water
  5. additionThe combined aqueous phase was treated with glacial acetic acid to pH 5
  6. customto precipitate a crude product
  7. customFurther crude product was obtained
  8. extractionby extracting the ether
  9. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-660ba3151f6b40d89065c2d132e6651e
Source dataset
uspto-grants-1992_06
Patent number
US05118686

Reaction notes

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