HCID 18932921, compound → HCID 178457518, compound

HRID 1756705Notes

Reaction equation

HRID 1756705 reaction equation
[CH2:1]([N:4]1C(=O)C(C(OCC)=O)=C[N:6]=[C:5]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:2]=[CH2:3].Cl.C(NC(=N)C1C=CC=CC=1)C=C>[OH-].[Na+]>[CH2:1]([NH:4][C:5](=[NH:6])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 18932921HCID 18932921, compoundHCID 178457519HCID 178457519, compound2×

Product 1

HCID 178457518HCID 178457518, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 1-allyl-2-phenylpyrimidin-6(1H)-one-5-carboxylate. The free base of N-allylbenzamidine hydrochloride was generated by dissolving N-allylbenzamidine hydrochloride (79.7 g) in 1N sodium hydroxide. The free base was then extracted into dichloromethane, which was dried and evaporated to provide N-allylbenzamidine (65.2 g). This was added to diethyl ethoxymethylenemalonate (78 mL) in ethanol (50 mL). The resulting solution was heated at 120° C. for 2 hours. 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 (62.5 g) as a white solid; 300 HHz 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-a796e0b35d524852a875d3cc17cb315c
Source dataset
uspto-grants-1995_08
Patent number
US05441960

Reaction notes

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