2-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acid → HCID 21092728, compound

HRID 1348990Notes

Reaction equation

HRID 1348990 reaction equation
FC(F)(F)C(O)=[O:4].[CH3:8][C:9]1[N:10]=[C:11]([S:14]([N:17]2[CH2:22][CH2:21][NH:20][C:19](=O)[CH2:18]2)(=[O:16])=[O:15])[S:12][CH:13]=1.[N:24]1([CH2:33][C:34](O)=[O:35])[CH:32]=[C:30]([CH3:31])[C:28](=[O:29])[NH:27][C:25]1=[O:26].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:8][C:9]1[N:10]=[C:11]([S:14]([N:17]2[CH2:22][CH2:21][N:20]([C:34](=[O:35])[CH2:33][N:24]3[CH:32]=[C:30]([CH3:31])[C:28](=[O:29])[NH:27][C:25]3=[O:26])[CH2:19][C:18]2=[O:4])(=[O:16])=[O:15])[S:12][CH:13]=1

Participants

5

Reactant 3

HCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 2724699PyBOPHCID 69038924HCID 69038924, compound

Product 1

HCID 21092728HCID 21092728, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3 mL of DMF, were added 0.30 g (0.8 mmol) of 4-(4-methyl-thiazole-2-sulfonyl)-piperazin-2-one trifluoroacetic acid salt, 0.147 g (0.8 mmol) of (thymin-1-yl)-acetic acid and 0.458 g of PyBOP. The reaction mixture was stirred for 4 hours at room temperature. Almost of the solvent was removed in vacuo and the residue was dissolved in methylene chloride. The solution was washed with saturated sodium bicarbonate solution, water, 1N HCl, water and brine sequencially. The organic layer was concentrated and column chromatographed on silicagel to give 0.19 g (56%) of the title compound.

Workup

  1. customAlmost of the solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washThe solution was washed with saturated sodium bicarbonate solution, water, 1N HCl, water and brine sequencially
  4. concentrationThe organic layer was concentrated
  5. customcolumn chromatographed on silicagel

Sources & evidence

ORD record
ord-8d6427db6f4c4c5180c6c134ee3e159f
Source dataset
uspto-grants-2007_05
Patent number
US07211668B2

Reaction notes

Loading…