Guanidine Hydrochloride → 2-Amino-6-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-4-pyrimidone

HRID 1589145Notes

Reaction equation

HRID 1589145 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([CH3:23])[NH:16][C:15]([CH2:24][O:25][CH2:26][C:27](=O)[CH2:28][C:29](OCC)=[O:30])=[C:14]1[C:35]([O:37][CH2:38][CH3:39])=[O:36].N12CCCC1=NCCC2>C(O)C>[NH2:4][C:3]1[NH:5][C:29](=[O:30])[CH:28]=[C:27]([CH2:26][O:25][CH2:24][C:15]2[NH:16][C:17]([CH3:23])=[C:18]([C:19]([O:21][CH3:22])=[O:20])[CH:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[Cl:6])[C:14]=2[C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:2]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 70044209Ethyl 4-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetoacetate

Product 1

HCID 1363872922-Amino-6-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-4-pyrimidoneYield 23.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of guanidine hydrochloride (0.20 g), ethyl 4-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetoacetate (0.99 g), and 1,5-diazabicyclo[4.3.0]non-5-ene (0.30 g) in ethanol (50 ml) was stirred at room temperature for 5 days and then evaporated. The residue was dissolved in chloroform and washed with 2M hydrochloric acid, 10% aqueous sodium carbonate, and water, dried (MgSO4), and evaporated. The residual solid was recrystallised from ethyl acetate to give the title compound (0.23 g), m.p. 185°-187° C. Found: C,56.08; H,5.14; N,11.33. C23H25ClN4O6 requires C,56.50; H,5.15; N,11.46%.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with 2M hydrochloric acid, 10% aqueous sodium carbonate, and water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residual solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-e08c39c1377e41cbadf773f8065cfdc4
Source dataset
uspto-grants-1986_02
Patent number
US04568677

Reaction notes

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