Acetic Acid → 3-(2-Thienyl)propyl 2-(2-furyl)-4-(4-methyl-3-nitrophenyl)-6-[(2-(1-piperidinyl)ethoxy)methyl]-1,4-dihydropyrimidine-5-carboxylate

HRID 324787Notes

Reaction equation

HRID 324787 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][C:27]=1[N+:34]([O-:36])=[O:35].Cl.[C:38]([C:41]1[O:42][CH:43]=[CH:44][CH:45]=1)(=[NH:40])[NH2:39].N1CCOCC1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)C>[O:42]1[CH:43]=[CH:44][CH:45]=[C:41]1[C:38]1[NH:40][C:11]([CH2:10][O:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[O:14])[CH:30]([C:29]2[CH:32]=[CH:33][C:26]([CH3:25])=[C:27]([N+:34]([O-:36])=[O:35])[CH:28]=2)[N:39]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8083MorpholineHCID 24436Sodium SulfateHCID 17989983-Nitro-p-tolualdehydeHCID 12231049Furan-2-carboximidamide hydrochlorideHCID 220055603-(2-Thienyl)propyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate

Product 1

HCID 220055673-(2-Thienyl)propyl 2-(2-furyl)-4-(4-methyl-3-nitrophenyl)-6-[(2-(1-piperidinyl)ethoxy)methyl]-1,4-dihydropyrimidine-5-carboxylateYield 1.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-(2-thienyl)propyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate (4.0 g, 11.32 mmol), 4-methyl-3-nitrobenzaldehyde (1.87 g, 11.32 mmol), 2-amidinofuran hydrochloride (1.65 g, 11.32 mmol), morpholine (1.48 ml, 16.98 mmol), acetic acid (1.29 ml, 22.64 mmol), and sodium sulfate (3.21 g, 22.64 mmol) was stirred in ethanol (45 ml) for 1 hour at room temperature and then heated to 40° C. for 9 days. The ethanol was removed in vacuo and ethyl acetate was added to the residue. The filtrate was washed with water, sodium hydrogen carbonate solution and brine, dried and evaporated to yield an oil. The oil was further purified by flash chromatography and RP-HPLC to give the title compound (120 mg) as an oil. Electrospray MS m/z 593 [M+H]+, m/z 297 [M+2H]++.

Workup

  1. customThe ethanol was removed in vacuo and ethyl acetate
  2. additionwas added to the residue
  3. washThe filtrate was washed with water, sodium hydrogen carbonate solution and brine
  4. customdried
  5. customevaporated
  6. customto yield an oil
  7. customThe oil was further purified by flash chromatography and RP-HPLC

Sources & evidence

ORD record
ord-c193b191ed3e45d28e9d90b5f1ec7667
Source dataset
uspto-grants-2001_04
Patent number
US06218538B1

Reaction notes

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