HCID 178457519, compound → HCID 178457518, compound

HRID 1656502Notes

Reaction equation

HRID 1656502 reaction equation
Cl.[CH2:2]([NH:5][C:6](=[NH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:3]=[CH2:4]>[OH-].[Na+]>[CH2:2]([NH:5][C:6](=[NH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:3]=[CH2:4]

Participants

3

Reactant 1

HCID 178457519HCID 178457519, compound2×

Product 1

HCID 178457518HCID 178457518, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The free base of N-allyl benzamidine hydrochloride was generated by dissolving N-allyl benzamidine hydrochloride (79.7 g) in 1N sodium hydroxide. The free base was then extracted into dichloromethane, which was dried and evaporated to provide N-allyl benzamidine (65.2 g). This was added to diethyl ethoxymethylene malonate (78 mL) in ethanol (50 mL). The resulting solution was heated at 120° C. for 2 h. The solution was cooled, diluted with ethyl acetate, washed (saturated ammonium chloride, water), dried, and evaporated to give a solid, which was collected and washed two times with ether:hexane (1:1), to provide ethyl 1-allyl-2-phenylpyrimidin-6(1H)-one-5-carboxylate as a white solid (62.5 g); 300 MHz NMR: 8.56 (s,1), 7.54 (m,5), 5.80 (m,1), 5.09 (d,1), 4.82 (d,1), 4.47 (d,2), 4.28 (q,2), 1.28 (t,3).

Workup

  1. extractionThe free base was then extracted into dichloromethane, which
  2. customwas dried
  3. customevaporated

Sources & evidence

ORD record
ord-3b0fb5b09c07460cb8192a74f97cc094
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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