N,N-Diethylaniline → 3-(2-Heptyloxycarbonyl)-2,6-dimethyl-5-(3-methyl-2-butenyloxycarbonyl)-4-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrimidine

HRID 2119166Notes

Reaction equation

HRID 2119166 reaction equation
C(N(CC)CC)C.[CH3:8][CH:9]1[N:14]=[C:13]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[C:12]([C:27]([O:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])=[O:28])=[C:11]([CH3:35])[NH:10]1.C(N(CC)C1C=CC=CC=1)C.C(O)C#CCCCC.[Cl:55][C:56]([O:58][CH:59]([CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH3:60])=[O:57]>O1CCCC1.ClC(OC(Cl)(Cl)Cl)=O>[Cl:55][C:56]([O:58][CH:59]([CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH3:60])=[O:57].[CH3:60][CH:59]([O:58][C:56]([N:14]1[CH:13]([C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)[C:12]([C:27]([O:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])=[O:28])=[C:11]([CH3:35])[N:10]=[C:9]1[CH3:8])=[O:57])[CH2:61][CH2:62][CH2:63][CH2:64][CH3:65]

Participants

9

Reactant 5

HCID 7061N,N-DiethylanilineHCID 8471TriethylamineHCID 5351112-Heptyn-1-olHCID 201911132,6-Dimethyl-5-(3-methyl-2-butenyloxycarbonyl)-4-(3,4,5-trimethoxyphenyl)-dihydropyrimidineHCID 214878432-Heptyl chloroformate

Product 2

HCID 214878432-Heptyl chloroformateHCID 540167473-(2-Heptyloxycarbonyl)-2,6-dimethyl-5-(3-methyl-2-butenyloxycarbonyl)-4-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrimidineYield 69%

Reagents, catalysts & solvents 2

HCID 10426DiphosgeneCatalystHCID 8028TetrahydrofuranSolvent4×

Procedure

0.5 ml of Triethylamine was added to a solution of 200 mg of 2,6-dimethyl-5-(3-methyl-2-butenyloxycarbonyl)-4-(3,4,5-trimethoxyphenyl)-dihydropyrimidine in 5 ml of tetrahydrofuran (THF) and 2-heptyl chloroformate dissolved in 6 ml of THF was added dropwise. The 2-heptyl chloroformate was prepared by adding 0.25 ml of N,N-diethylaniline dissolved in 2 ml of THF to a solution of 0.15 g of 2-heptyn-1-ol and 0.1 mg of trichloromethyl chloroformate in 4 ml of THF in a separate reaction vessel. After stirring at room temperature for 1 hr, the reaction mixture was concentrated under reduced pressure. The residue was purified on silica gel by column chromatography (silica gel 20 g, eluant:benzene/ethyl acetate 9:1) to obtain 187 mg (69% yield) of title product.

Workup

  1. additionwas added dropwise
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified on silica gel by column chromatography (silica gel 20 g, eluant:benzene/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-c37654dacc504cea930d348b925596f8
Source dataset
uspto-grants-1987_07
Patent number
US04683234

Reaction notes

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