Dihydrouracil → 3-{4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzyl}-dihydro-pyrimidine-2,4-dione

HRID 2100692Notes

Reaction equation

HRID 2100692 reaction equation
[CH3:1][C:2]1[C:3]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=2)=[CH2:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.CS(Cl)(=O)=O.[NH:31]1[CH2:36][CH2:35][C:34](=[O:37])[NH:33][C:32]1=[O:38].[H-].[Na+]>CCN(CC)CC>[CH3:1][C:2]1[C:3]([C:16]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][N:33]3[C:34](=[O:37])[CH2:35][CH2:36][NH:31][C:32]3=[O:38])=[CH:22][CH:23]=2)=[CH2:17])=[CH:4][C:5]2[C:6]([CH3:14])([CH3:15])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 649DihydrouracilHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 57799975{4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenyl}-methanol

Product 1

HCID 114645913-{4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzyl}-dihydro-pyrimidine-2,4-dioneYield 55%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Adopting the procedure outlined for example 9 using 40.0 mg (0.12 mmol) of {4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenyl}-methanol, 0.05 mL of methanesulfonyl chloride, 0.10 mL of NEt3, 300 mg of dihydropyrimidine-2,4-dione, and 63 mg of NaH, 28.4 mg of the product was obtained.

Sources & evidence

ORD record
ord-03dea93d145b44c683ca3443f27ef6df
Source dataset
uspto-grants-2009_08
Patent number
US07572816B2

Reaction notes

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